CH617927A5 - - Google Patents
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- Publication number
- CH617927A5 CH617927A5 CH460679A CH460679A CH617927A5 CH 617927 A5 CH617927 A5 CH 617927A5 CH 460679 A CH460679 A CH 460679A CH 460679 A CH460679 A CH 460679A CH 617927 A5 CH617927 A5 CH 617927A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- derivatives
- oxyphenylbutazone
- bis
- general formula
- Prior art date
Links
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical class O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 16
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 13
- -1 formyloxy group Chemical group 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- 230000003110 anti-inflammatory effect Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 206010047139 Vasoconstriction Diseases 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 4
- 230000025033 vasoconstriction Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- 208000017520 skin disease Diseases 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 206010061218 Inflammation Diseases 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DKAFBCPTNDSPOD-UHFFFAOYSA-N bis(4-phenyldiazenylphenyl) hexanedioate Chemical compound C=1C=C(N=NC=2C=CC=CC=2)C=CC=1OC(=O)CCCCC(=O)OC(C=C1)=CC=C1N=NC1=CC=CC=C1 DKAFBCPTNDSPOD-UHFFFAOYSA-N 0.000 description 2
- GAKMQHDJQHZUTJ-ULHLPKEOSA-N fluocortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O GAKMQHDJQHZUTJ-ULHLPKEOSA-N 0.000 description 2
- 229960003973 fluocortolone Drugs 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 239000002085 irritant Substances 0.000 description 2
- 231100000021 irritant Toxicity 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 description 2
- 230000037311 normal skin Effects 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 229960000649 oxyphenbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical class O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 125000004149 thio group Chemical group *S* 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ITTFEPALADGOBD-UHFFFAOYSA-N 2-butylpropanedioyl dichloride Chemical compound CCCCC(C(Cl)=O)C(Cl)=O ITTFEPALADGOBD-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
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 206010012455 Dermatitis exfoliative Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020565 Hyperaemia Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 201000009053 Neurodermatitis Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241001303601 Rosacea Species 0.000 description 1
- 208000028990 Skin injury Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- BEYOBVMPDRKTNR-UHFFFAOYSA-N chembl79759 Chemical compound C1=CC(O)=CC=C1N=NC1=CC=CC=C1 BEYOBVMPDRKTNR-UHFFFAOYSA-N 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229940117173 croton oil Drugs 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- OJAGAAVUZKMVGX-UHFFFAOYSA-N ethyl acetate;pyridine Chemical compound CCOC(C)=O.C1=CC=NC=C1 OJAGAAVUZKMVGX-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 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
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000018937 joint inflammation Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical class ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 201000004700 rosacea Diseases 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
- C07D231/34—Oxygen atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2436882A DE2436882A1 (de) | 1974-07-29 | 1974-07-29 | Neue oxyphenylbutazon-derivate und ihre herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617927A5 true CH617927A5 (en, 2012) | 1980-06-30 |
Family
ID=5922046
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH989675A CH617926A5 (en, 2012) | 1974-07-29 | 1975-07-29 | |
| CH460679A CH617927A5 (en, 2012) | 1974-07-29 | 1979-05-17 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH989675A CH617926A5 (en, 2012) | 1974-07-29 | 1975-07-29 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3968219A (en, 2012) |
| JP (1) | JPS5136452A (en, 2012) |
| AT (1) | AT344689B (en, 2012) |
| AU (1) | AU8332175A (en, 2012) |
| BE (1) | BE831855A (en, 2012) |
| CA (1) | CA1062264A (en, 2012) |
| CH (2) | CH617926A5 (en, 2012) |
| CS (1) | CS197252B2 (en, 2012) |
| DD (1) | DD122533A5 (en, 2012) |
| DE (1) | DE2436882A1 (en, 2012) |
| DK (1) | DK137009C (en, 2012) |
| ES (1) | ES439810A1 (en, 2012) |
| FR (1) | FR2280374A1 (en, 2012) |
| GB (1) | GB1519498A (en, 2012) |
| HU (1) | HU170518B (en, 2012) |
| IE (1) | IE41639B1 (en, 2012) |
| IL (1) | IL47768A (en, 2012) |
| NL (1) | NL7509060A (en, 2012) |
| SE (1) | SE415252B (en, 2012) |
| SU (1) | SU593662A3 (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9915184D0 (en) * | 1999-06-29 | 1999-09-01 | Viral As A | Compounds |
| IL142037A0 (en) * | 2001-03-15 | 2002-03-10 | Agis Ind 1983 Ltd | Pharmaceutical compositions containing a non-steroidal anti-inflammatory drug |
| WO2005107748A2 (en) * | 2004-05-12 | 2005-11-17 | A-Viral Asa | Method of tonic treatment with oxyphenbutazone derivatives |
| US8729108B2 (en) * | 2008-06-17 | 2014-05-20 | Christopher J Dannaker | Waterborne topical compositions for the delivery of active ingredients such as azelaic acid |
| US20130071489A1 (en) | 2010-03-26 | 2013-03-21 | Galderma Research & Development Snc | Methods and compositions for safe and effective treatment of erythema |
| MX2014004383A (es) | 2011-10-19 | 2014-11-12 | Galderma Sa | Metodo para reducir el enrojecimiento facial asociado con el uso sistemico de inhibidores de fosfodiesterasa tipo 5. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR5404M (en, 2012) * | 1965-09-08 | 1967-09-25 | ||
| FR2054447B1 (en, 2012) * | 1969-07-03 | 1973-06-08 | Synthelabo |
-
1974
- 1974-07-29 DE DE2436882A patent/DE2436882A1/de not_active Withdrawn
-
1975
- 1975-07-17 CS CS755081A patent/CS197252B2/cs unknown
- 1975-07-23 IL IL47768A patent/IL47768A/xx unknown
- 1975-07-23 AU AU83321/75A patent/AU8332175A/en not_active Expired
- 1975-07-23 IE IE1650/75A patent/IE41639B1/en unknown
- 1975-07-24 SU SU752157426A patent/SU593662A3/ru active
- 1975-07-25 DD DD187483A patent/DD122533A5/xx unknown
- 1975-07-28 GB GB31409/75A patent/GB1519498A/en not_active Expired
- 1975-07-28 US US05/599,397 patent/US3968219A/en not_active Expired - Lifetime
- 1975-07-28 HU HUSC528A patent/HU170518B/hu unknown
- 1975-07-28 SE SE7508543A patent/SE415252B/xx unknown
- 1975-07-28 AT AT583675A patent/AT344689B/de not_active IP Right Cessation
- 1975-07-29 FR FR7523604A patent/FR2280374A1/fr active Granted
- 1975-07-29 ES ES439810A patent/ES439810A1/es not_active Expired
- 1975-07-29 CA CA232,437A patent/CA1062264A/en not_active Expired
- 1975-07-29 DK DK344375A patent/DK137009C/da active
- 1975-07-29 JP JP50092462A patent/JPS5136452A/ja active Pending
- 1975-07-29 CH CH989675A patent/CH617926A5/de not_active IP Right Cessation
- 1975-07-29 NL NL7509060A patent/NL7509060A/xx not_active Application Discontinuation
- 1975-07-29 BE BE158718A patent/BE831855A/xx unknown
-
1979
- 1979-05-17 CH CH460679A patent/CH617927A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7509060A (nl) | 1976-02-02 |
| IE41639B1 (en) | 1980-02-13 |
| DE2436882A1 (de) | 1976-02-19 |
| SE415252B (sv) | 1980-09-22 |
| US3968219A (en) | 1976-07-06 |
| ES439810A1 (es) | 1977-04-16 |
| DD122533A5 (en, 2012) | 1976-10-12 |
| GB1519498A (en) | 1978-07-26 |
| CH617926A5 (en, 2012) | 1980-06-30 |
| SE7508543L (sv) | 1976-01-30 |
| DK137009B (da) | 1978-01-02 |
| CA1062264A (en) | 1979-09-11 |
| FR2280374B1 (en, 2012) | 1980-04-30 |
| CS197252B2 (en) | 1980-04-30 |
| IL47768A (en) | 1979-10-31 |
| ATA583675A (de) | 1977-12-15 |
| HU170518B (en, 2012) | 1977-06-28 |
| AU8332175A (en) | 1977-01-27 |
| JPS5136452A (en, 2012) | 1976-03-27 |
| FR2280374A1 (fr) | 1976-02-27 |
| DK344375A (da) | 1976-01-30 |
| IE41639L (en) | 1976-01-29 |
| IL47768A0 (en) | 1975-10-15 |
| BE831855A (fr) | 1976-01-29 |
| DK137009C (da) | 1978-05-22 |
| AT344689B (de) | 1978-08-10 |
| SU593662A3 (ru) | 1978-02-15 |
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