CS244669B2 - Production method of the new s,s'-alkyle-di(dithioalkanoles di(dithioalkanol lower alkyletheres)and-di(dithioalkanolesters) - Google Patents
Production method of the new s,s'-alkyle-di(dithioalkanoles di(dithioalkanol lower alkyletheres)and-di(dithioalkanolesters) Download PDFInfo
- Publication number
- CS244669B2 CS244669B2 CS82784A CS78482A CS244669B2 CS 244669 B2 CS244669 B2 CS 244669B2 CS 82784 A CS82784 A CS 82784A CS 78482 A CS78482 A CS 78482A CS 244669 B2 CS244669 B2 CS 244669B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- compound
- compounds
- dithioalkanol
- independently
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000005011 alkyl ether group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 230000003308 immunostimulating effect Effects 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- -1 thio compound Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000427 antigen Substances 0.000 description 8
- 102000036639 antigens Human genes 0.000 description 8
- 108091007433 antigens Proteins 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229910052804 chromium Inorganic materials 0.000 description 6
- 239000011651 chromium Substances 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000028993 immune response Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 210000004989 spleen cell Anatomy 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 102000014150 Interferons Human genes 0.000 description 4
- 108010050904 Interferons Proteins 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 229940079322 interferon Drugs 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 210000003743 erythrocyte Anatomy 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 230000016396 cytokine production Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000008348 humoral response Effects 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 210000004698 lymphocyte Anatomy 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 210000001539 phagocyte Anatomy 0.000 description 2
- 230000007505 plaque formation Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 210000000952 spleen Anatomy 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000003319 supportive effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000005951 type IV hypersensitivity Effects 0.000 description 2
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 2
- 238000002255 vaccination Methods 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 201000006082 Chickenpox Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- 208000029462 Immunodeficiency disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010069582 Progressive vaccinia Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 206010046980 Varicella Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000011360 adjunctive therapy Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000000735 allogeneic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 230000003053 immunization Effects 0.000 description 1
- 238000002649 immunization Methods 0.000 description 1
- 230000007813 immunodeficiency Effects 0.000 description 1
- 230000016784 immunoglobulin production Effects 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
- BYGOPQKDHGXNCD-UHFFFAOYSA-N tripotassium;iron(3+);hexacyanide Chemical compound [K+].[K+].[K+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] BYGOPQKDHGXNCD-UHFFFAOYSA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000003039 volatile agent 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
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/105—Persulfides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8103513 | 1981-02-05 |
Publications (2)
Publication Number | Publication Date |
---|---|
CS78482A2 CS78482A2 (en) | 1985-09-17 |
CS244669B2 true CS244669B2 (en) | 1986-08-14 |
Family
ID=10519462
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS82784A CS244669B2 (en) | 1981-02-05 | 1982-02-04 | Production method of the new s,s'-alkyle-di(dithioalkanoles di(dithioalkanol lower alkyletheres)and-di(dithioalkanolesters) |
Country Status (20)
Country | Link |
---|---|
US (1) | US4407825A (de) |
EP (1) | EP0058134B1 (de) |
JP (1) | JPS57149266A (de) |
AT (1) | ATE5535T1 (de) |
AU (1) | AU547237B2 (de) |
CA (1) | CA1183549A (de) |
CS (1) | CS244669B2 (de) |
DE (1) | DE3260015D1 (de) |
DK (1) | DK47082A (de) |
ES (1) | ES509331A0 (de) |
FI (1) | FI75802C (de) |
GR (1) | GR74737B (de) |
HU (1) | HU187638B (de) |
IE (1) | IE52243B1 (de) |
IL (1) | IL64927A (de) |
MY (1) | MY8700185A (de) |
NZ (1) | NZ199637A (de) |
PH (1) | PH22985A (de) |
PT (1) | PT74380B (de) |
ZA (1) | ZA82759B (de) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8405896D0 (en) * | 1984-03-07 | 1984-04-11 | Sandoz Ltd | Organic compounds |
FR2647117A1 (de) * | 1989-05-18 | 1990-11-23 | Elf France | |
US5391785A (en) * | 1990-01-16 | 1995-02-21 | La Jolla Pharmaceutial Company | Intermediates for providing functional groups on the 5' end of oligonucleotides |
US9325041B2 (en) | 2012-03-22 | 2016-04-26 | The Boeing Company | Redox polymer energy storage system |
US9896922B2 (en) | 2012-12-21 | 2018-02-20 | Praxair Technology, Inc. | System and apparatus for creating a liquid carbon dioxide fracturing fluid |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2806065A (en) * | 1952-03-24 | 1957-09-10 | Bayer Ag | Manufacture of bis-(b-hydroxyalkyl-) polysulfides |
DE1093790B (de) * | 1958-09-24 | 1960-12-01 | Bayer Ag | Verfahren zur Herstellung von hydroxylgruppenhaltigen Disulfiden |
BE595533A (de) * | 1959-10-01 | |||
FR1487364A (fr) * | 1966-05-09 | 1967-07-07 | Aquitaine Petrole | Procédé de préparation de glycols polythioéthers |
GB1307227A (en) | 1969-08-08 | 1973-02-14 | Orsymonde | Pharmaceutical compositions comprising dicarboxylic acids and their derivatives |
CH580384A5 (de) | 1973-08-27 | 1976-10-15 | Sandoz Ag | |
US4258212A (en) * | 1979-12-17 | 1981-03-24 | The B. F. Goodrich Company | Process for preparing polysulfide chain terminator |
-
1982
- 1982-01-28 EP EP82810038A patent/EP0058134B1/de not_active Expired
- 1982-01-28 DE DE8282810038T patent/DE3260015D1/de not_active Expired
- 1982-01-28 AT AT82810038T patent/ATE5535T1/de not_active IP Right Cessation
- 1982-01-29 FI FI820292A patent/FI75802C/fi not_active IP Right Cessation
- 1982-01-29 US US06/344,175 patent/US4407825A/en not_active Expired - Fee Related
- 1982-02-03 GR GR67191A patent/GR74737B/el unknown
- 1982-02-03 IL IL64927A patent/IL64927A/xx unknown
- 1982-02-03 DK DK47082A patent/DK47082A/da not_active Application Discontinuation
- 1982-02-03 AU AU80163/82A patent/AU547237B2/en not_active Ceased
- 1982-02-03 PT PT74380A patent/PT74380B/pt unknown
- 1982-02-03 NZ NZ199637A patent/NZ199637A/en unknown
- 1982-02-03 PH PH26826A patent/PH22985A/en unknown
- 1982-02-04 ES ES509331A patent/ES509331A0/es active Granted
- 1982-02-04 HU HU82339A patent/HU187638B/hu not_active IP Right Cessation
- 1982-02-04 JP JP57017384A patent/JPS57149266A/ja active Pending
- 1982-02-04 IE IE245/82A patent/IE52243B1/en unknown
- 1982-02-04 CA CA000395528A patent/CA1183549A/en not_active Expired
- 1982-02-04 CS CS82784A patent/CS244669B2/cs unknown
- 1982-02-05 ZA ZA82759A patent/ZA82759B/xx unknown
-
1987
- 1987-12-30 MY MY185/87A patent/MY8700185A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
CA1183549A (en) | 1985-03-05 |
US4407825A (en) | 1983-10-04 |
FI820292L (fi) | 1982-08-06 |
AU547237B2 (en) | 1985-10-10 |
PT74380B (en) | 1983-12-07 |
ES8307731A1 (es) | 1983-08-16 |
ES509331A0 (es) | 1983-08-16 |
ZA82759B (en) | 1983-09-28 |
MY8700185A (en) | 1987-12-31 |
DE3260015D1 (en) | 1984-01-12 |
JPS57149266A (en) | 1982-09-14 |
EP0058134B1 (de) | 1983-12-07 |
IE52243B1 (en) | 1987-08-19 |
HU187638B (en) | 1986-02-28 |
FI75802B (fi) | 1988-04-29 |
CS78482A2 (en) | 1985-09-17 |
PT74380A (en) | 1982-03-01 |
DK47082A (da) | 1982-08-06 |
IE820245L (en) | 1982-08-05 |
GR74737B (de) | 1984-07-11 |
IL64927A0 (en) | 1982-04-30 |
PH22985A (en) | 1989-02-24 |
FI75802C (fi) | 1988-08-08 |
AU8016382A (en) | 1982-08-12 |
EP0058134A1 (de) | 1982-08-18 |
IL64927A (en) | 1986-01-31 |
ATE5535T1 (de) | 1983-12-15 |
NZ199637A (en) | 1984-11-09 |
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