DE2102586C2 - Verwendung von Vitamin A-Säureamiden - Google Patents
Verwendung von Vitamin A-SäureamidenInfo
- Publication number
- DE2102586C2 DE2102586C2 DE2102586A DE2102586A DE2102586C2 DE 2102586 C2 DE2102586 C2 DE 2102586C2 DE 2102586 A DE2102586 A DE 2102586A DE 2102586 A DE2102586 A DE 2102586A DE 2102586 C2 DE2102586 C2 DE 2102586C2
- Authority
- DE
- Germany
- Prior art keywords
- vitamin
- acid
- group
- acid amides
- well
- Prior art date
- 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
Links
- 229930002330 retinoic acid Natural products 0.000 title claims description 27
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 title claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 201000009030 Carcinoma Diseases 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- 201000004624 Dermatitis Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 210000004400 mucous membrane Anatomy 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000009897 systematic effect Effects 0.000 claims description 2
- 238000011282 treatment Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002775 capsule Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- -1 η-butyl Chemical group 0.000 description 5
- 235000019484 Rapeseed oil Nutrition 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- WKYDOCGICAMTKE-NBIQJRODSA-N n-ethyl retinamide Chemical compound CCNC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C WKYDOCGICAMTKE-NBIQJRODSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000945 filler 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
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VMSLCPKYRPDHLN-UHFFFAOYSA-N (R)-Humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 239000004258 Ethoxyquin Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019285 ethoxyquin Nutrition 0.000 description 1
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- 229940093500 ethoxyquin Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000009121 systemic therapy Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH142870A CH529742A (de) | 1970-02-02 | 1970-02-02 | Verfahren zur Herstellung von Vitamin-A-Säureamiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2102586A1 DE2102586A1 (de) | 1971-08-12 |
| DE2102586C2 true DE2102586C2 (de) | 1985-03-14 |
Family
ID=4210229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2102586A Expired DE2102586C2 (de) | 1970-02-02 | 1971-01-20 | Verwendung von Vitamin A-Säureamiden |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS544948B1 (cs) |
| AT (1) | AT303274B (cs) |
| BE (1) | BE762345A (cs) |
| CA (1) | CA963910A (cs) |
| CH (1) | CH529742A (cs) |
| DE (1) | DE2102586C2 (cs) |
| DK (1) | DK136311B (cs) |
| ES (1) | ES387834A1 (cs) |
| FI (1) | FI52715C (cs) |
| FR (1) | FR2081477B1 (cs) |
| GB (1) | GB1283887A (cs) |
| IE (1) | IE35133B1 (cs) |
| IL (1) | IL35987A (cs) |
| NL (1) | NL168415C (cs) |
| NO (1) | NO133802C (cs) |
| SE (1) | SE373133B (cs) |
| YU (1) | YU34355B (cs) |
| ZA (1) | ZA71142B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2300107C2 (de) * | 1973-01-03 | 1982-03-11 | Basf Ag, 6700 Ludwigshafen | Vitamin A-Säureanilid-4-carbonsäureäthylester, Verfahren zu seiner Herstellung und diesen enthaltende Zubereitungen |
| US4310546A (en) * | 1978-07-31 | 1982-01-12 | Johnson & Johnson | Novel retinoids and their use in preventing carcinogenesis |
| DE2843915A1 (de) * | 1978-10-07 | 1980-04-24 | Basf Ag | N-benzoyl-retinylamine |
| DE2843870A1 (de) * | 1978-10-07 | 1980-04-24 | Basf Ag | N-hydroxypropylamide der all-e- und 13-z-retinsaeure |
| DE3002545A1 (de) * | 1980-01-25 | 1981-07-30 | Basf Ag, 6700 Ludwigshafen | 5-amino-tetrazol-derivate von retinsaeuren, ihre herstellung und diese enthaltende pharmazeutische zubereitungen |
| CH651007A5 (de) * | 1982-06-24 | 1985-08-30 | Hoffmann La Roche | Polyenverbindungen. |
| DE69606514T2 (de) * | 1995-09-01 | 2000-09-14 | Dsm N.V., Heerlen | Derivate von sphingoid basen auf basis von retinoylamid |
| US7566808B2 (en) | 2004-02-17 | 2009-07-28 | President And Fellows Of Harvard College | Management of ophthalmologic disorders, including macular degeneration |
| CN101048375B (zh) * | 2004-07-09 | 2012-12-05 | 帝斯曼知识产权资产管理有限公司 | 视黄酸的氨基、氨基酸或肽共轭物 |
| KR100837186B1 (ko) * | 2006-09-29 | 2008-06-13 | (주)아모레퍼시픽 | 항노화 효과를 나타내는 레티노익산 유도체 및 이의제조방법 |
| US11148998B2 (en) | 2017-05-23 | 2021-10-19 | The Regents Of The University Of Michigan | Dimethyl-nonatetraenyl-trimethyl-cyclohexyl compounds and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH195065A (de) * | 1936-11-23 | 1938-01-15 | Int Suiker En Alcohol Compagni | Einrichtung an Vacuumapparaten zum Erleichtern des Auswechselns einzelner Röhren. |
| FR1297730A (fr) * | 1960-11-04 | 1962-07-06 | Hoffmann La Roche | Préparation cosmétique |
| NL257621A (cs) * | 1959-11-23 | |||
| FR1320153A (fr) * | 1962-01-22 | 1963-03-08 | Sumitomo Chemical Co | Procédé de production de composés dérivés de l'acide de vitamine a 2-trans |
-
1970
- 1970-02-02 CH CH142870A patent/CH529742A/de not_active IP Right Cessation
- 1970-12-09 FI FI703317A patent/FI52715C/fi active
- 1970-12-15 NL NLAANVRAGE7018260,A patent/NL168415C/xx not_active IP Right Cessation
- 1970-12-28 YU YU3184/70A patent/YU34355B/xx unknown
-
1971
- 1971-01-11 ZA ZA710142A patent/ZA71142B/xx unknown
- 1971-01-12 IL IL35987A patent/IL35987A/xx unknown
- 1971-01-20 DE DE2102586A patent/DE2102586C2/de not_active Expired
- 1971-01-29 FR FR7103020A patent/FR2081477B1/fr not_active Expired
- 1971-01-29 DK DK40571AA patent/DK136311B/da not_active Application Discontinuation
- 1971-01-29 CA CA103,975A patent/CA963910A/en not_active Expired
- 1971-02-01 BE BE762345A patent/BE762345A/xx not_active IP Right Cessation
- 1971-02-01 AT AT79971A patent/AT303274B/de not_active IP Right Cessation
- 1971-02-01 ES ES387834A patent/ES387834A1/es not_active Expired
- 1971-02-01 JP JP356271A patent/JPS544948B1/ja active Pending
- 1971-02-01 NO NO343/71*[A patent/NO133802C/no unknown
- 1971-02-02 IE IE118/71A patent/IE35133B1/xx unknown
- 1971-02-02 SE SE7101274A patent/SE373133B/xx unknown
- 1971-04-19 GB GB20880/71A patent/GB1283887A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL168415B (nl) | 1981-11-16 |
| NL168415C (nl) | 1982-04-16 |
| GB1283887A (en) | 1972-08-02 |
| DK136311C (cs) | 1978-02-20 |
| IL35987A (en) | 1974-01-14 |
| IE35133L (en) | 1971-08-02 |
| NO133802C (cs) | 1976-06-30 |
| DE2102586A1 (de) | 1971-08-12 |
| SE373133B (cs) | 1975-01-27 |
| BE762345A (fr) | 1971-08-02 |
| ZA71142B (en) | 1971-10-27 |
| AT303274B (de) | 1972-11-27 |
| CA963910A (en) | 1975-03-04 |
| FR2081477A1 (cs) | 1971-12-03 |
| YU34355B (en) | 1979-07-10 |
| JPS544948B1 (cs) | 1979-03-12 |
| IE35133B1 (en) | 1975-11-26 |
| FI52715B (cs) | 1977-08-01 |
| ES387834A1 (es) | 1973-06-01 |
| FR2081477B1 (cs) | 1974-03-22 |
| FI52715C (fi) | 1977-11-10 |
| IL35987A0 (en) | 1971-03-24 |
| CH529742A (de) | 1972-10-31 |
| DK136311B (da) | 1977-09-26 |
| NL7018260A (cs) | 1971-08-04 |
| NO133802B (cs) | 1976-03-22 |
| YU318470A (en) | 1978-12-31 |
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