IE40523B1 - Novel benzylpyrimidines - Google Patents
Novel benzylpyrimidinesInfo
- Publication number
- IE40523B1 IE40523B1 IE1870/74A IE187074A IE40523B1 IE 40523 B1 IE40523 B1 IE 40523B1 IE 1870/74 A IE1870/74 A IE 1870/74A IE 187074 A IE187074 A IE 187074A IE 40523 B1 IE40523 B1 IE 40523B1
- Authority
- IE
- Ireland
- Prior art keywords
- sulphanilamido
- sulphonamides
- nhr
- sept
- pyrimidine
- Prior art date
Links
- OOLOAWZLPBDRJQ-UHFFFAOYSA-N 2-benzylpyrimidine Chemical class N=1C=CC=NC=1CC1=CC=CC=C1 OOLOAWZLPBDRJQ-UHFFFAOYSA-N 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 abstract 2
- 150000003456 sulfonamides Chemical class 0.000 abstract 2
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 abstract 1
- AMFSJVJTVJYFBE-UHFFFAOYSA-N 2-amino-n-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound CC1=C(C)ON=C1NS(=O)(=O)C1=CC=CC=C1N AMFSJVJTVJYFBE-UHFFFAOYSA-N 0.000 abstract 1
- AZVRQGHQVPBIHL-UHFFFAOYSA-N 2-amino-n-(4,5-dimethylpyrimidin-2-yl)benzenesulfonamide Chemical compound N1=C(C)C(C)=CN=C1NS(=O)(=O)C1=CC=CC=C1N AZVRQGHQVPBIHL-UHFFFAOYSA-N 0.000 abstract 1
- NHZLNPMOSADWGC-UHFFFAOYSA-N 4-amino-N-(2-quinoxalinyl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CN=C(C=CC=C2)C2=N1 NHZLNPMOSADWGC-UHFFFAOYSA-N 0.000 abstract 1
- ORWKAFKIAPHHBG-UHFFFAOYSA-N 4-amino-n-(4,5-dimethoxypyrimidin-2-yl)benzenesulfonamide Chemical compound N1=C(OC)C(OC)=CN=C1NS(=O)(=O)C1=CC=C(N)C=C1 ORWKAFKIAPHHBG-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 abstract 1
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 abstract 1
- 108010022394 Threonine synthase Proteins 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000001580 bacterial effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 102000004419 dihydrofolate reductase Human genes 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 229960000304 folic acid Drugs 0.000 abstract 1
- 235000019152 folic acid Nutrition 0.000 abstract 1
- 239000011724 folic acid Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- -1 pyrrolidino, piperidino Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 abstract 1
- 229960004306 sulfadiazine Drugs 0.000 abstract 1
- ZZORFUFYDOWNEF-UHFFFAOYSA-N sulfadimethoxine Chemical compound COC1=NC(OC)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 ZZORFUFYDOWNEF-UHFFFAOYSA-N 0.000 abstract 1
- 229960005404 sulfamethoxazole Drugs 0.000 abstract 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
- C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1484481 Compositions containing benzylpyrimidines F HOFFMANN-LA ROCHE & CO AG 11 Sept 1974 [12 Sept 1973] 39617/74 Heading A5B [Also in Division C2] An antibacterial composition contains a benzylpyrimidine of the formula: wherein R<SP>1</SP> and R<SP>2</SP> are (C 1 -C 3 ) alkyl or alkoxy, or (C 2 or C 3 ) alkenyl or alkenyloxy; Z is NO 2 , NH 2 , pyrrolo, pyrrolidino, piperidino, NHR<SP>4</SP>, -N(R<SP>4</SP>) 2 , -NHR<SP>5</SP>, -NR<SP>4</SP>R<SP>5</SP>, -NR<SP>4</SP>COOR<SP>4</SP>, -NHCOOR<SP>4</SP>, -NHCONHR<SP>3</SP>, -NHCSNHR<SP>3</SP>, -N 3 , -N=N-N(R<SP>4</SP>) 2 or -N(NO)R<SP>4</SP>, R<SP>3</SP> is H, (C 1 -C 3 ) alkyl or (C 2 -C 3 ) alkenyl and R<SP>5</SP> is acyl, and salts thereof; in association with a compatible pharmaceutical carrier. Compounds of the above formula inhibit bacterial dihydrofolate reductase and potentiate the antibacterial activity of sulphonamides with which they may be combined. Specified sulphonamides are sulphisoxazole, sulphadimethoxine, sulphamethoxazole, 4-sulphanilamido-5, 6-dimethoxy-pyrimidine, 2-sulphanilamido-4, 5- dimethyl-pyrimidine, sulphaquinoxaline, sulphadiazine sulphamonomethoxine and 2-sulphanilamido-4, 5-dimethylisoxazole. Other inhibitors for enzymes involved in the folic acid biosynthesis may also be incorporated in the compositions. They may be applied orally, rectally or parenterally.
[GB1484481A]
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE1983/77A IE40525B1 (en) | 1973-09-12 | 1974-09-09 | Hydrocinnamic acid nitriles |
| IE1982/77A IE40524B1 (en) | 1973-09-12 | 1974-09-09 | -cyano-hydrocinnamaldehyde acetals |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1305773A CH591456A5 (en) | 1973-09-12 | 1973-09-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE40523L IE40523L (en) | 1975-03-12 |
| IE40523B1 true IE40523B1 (en) | 1979-06-20 |
Family
ID=4388903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1870/74A IE40523B1 (en) | 1973-09-12 | 1974-09-09 | Novel benzylpyrimidines |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS6042238B2 (en) |
| AR (2) | AR207764A1 (en) |
| AT (1) | AT338797B (en) |
| BE (1) | BE819773A (en) |
| BR (1) | BR7407614D0 (en) |
| CA (1) | CA1037476A (en) |
| CH (1) | CH591456A5 (en) |
| CU (1) | CU34115A (en) |
| DD (2) | DD116824A5 (en) |
| DE (1) | DE2443682C2 (en) |
| DK (1) | DK135683B (en) |
| ES (7) | ES429949A1 (en) |
| FI (1) | FI58638C (en) |
| FR (1) | FR2242984B1 (en) |
| GB (3) | GB1484482A (en) |
| HK (1) | HK181A (en) |
| HU (1) | HU170427B (en) |
| IE (1) | IE40523B1 (en) |
| IL (1) | IL45510A (en) |
| LU (1) | LU70878A1 (en) |
| NL (1) | NL155827B (en) |
| NO (1) | NO140858C (en) |
| PH (1) | PH10643A (en) |
| PL (2) | PL99159B1 (en) |
| SE (1) | SE419443B (en) |
| SU (3) | SU577987A3 (en) |
| YU (3) | YU217874A (en) |
| ZA (1) | ZA745317B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4515948A (en) * | 1973-09-12 | 1985-05-07 | Hoffmann-La Roche Inc. | 2,4-Diamino-5-(4-amino and 4-dimethylamino-3,5-dimethoxy benzyl)pyrimidines |
| JPS5481278A (en) * | 1977-10-18 | 1979-06-28 | Wellcome Found | Manufacture of triiseccaminomethane |
| CH639273A5 (en) * | 1978-09-12 | 1983-11-15 | Hoffmann La Roche | DIURETIC MEANS. |
| CH658246A5 (en) * | 1981-11-09 | 1986-10-31 | Wellcome Found | METHOD FOR PRODUCING SUBSTITUTED 2,4-DIAMINO-5-BENZYLPYRIMIDINES. |
| DE3250132C2 (en) * | 1981-11-09 | 1997-01-16 | Mallinckrodt Veterinary Inc | 2,4-Di:amino-5-benzyl-pyrimidine derivs. prepn. |
| GB2180836A (en) * | 1985-09-27 | 1987-04-08 | William James Stephen Barker | Sunscreen |
| CA1300166C (en) * | 1987-12-03 | 1992-05-05 | Alfredo Guerrato | Process for the preparation of a benzoic acid ester |
| US4900859A (en) * | 1987-12-03 | 1990-02-13 | Hoffman-La Roche Inc. | Process for 4-dimethylamino-3,5-dimethoxybenzaldehyde |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1103931B (en) * | 1957-02-21 | 1961-04-06 | Wellcome Found | Process for the preparation of 2,4-diamino-5-benzylpyrimidine derivatives |
| US3485840A (en) * | 1964-11-12 | 1969-12-23 | Hoffmann La Roche | 2,4-diamino - 5 - (2',4',5'-substituted benzyl) pyrimidines,intermediates and processes |
-
1973
- 1973-09-12 CH CH1305773A patent/CH591456A5/xx not_active IP Right Cessation
-
1974
- 1974-01-01 AR AR255569A patent/AR207764A1/en active
- 1974-08-06 YU YU02178/74A patent/YU217874A/en unknown
- 1974-08-19 ZA ZA00745317A patent/ZA745317B/en unknown
- 1974-08-21 CA CA207,509A patent/CA1037476A/en not_active Expired
- 1974-08-21 IL IL45510A patent/IL45510A/en unknown
- 1974-09-02 FI FI2561/74A patent/FI58638C/en active
- 1974-09-03 NL NL7411685.A patent/NL155827B/en not_active IP Right Cessation
- 1974-09-04 DK DK468374AA patent/DK135683B/en unknown
- 1974-09-06 PL PL1974195308A patent/PL99159B1/en unknown
- 1974-09-06 PL PL1974173909A patent/PL97757B1/en unknown
- 1974-09-09 SE SE7411382A patent/SE419443B/en unknown
- 1974-09-09 PH PH16253A patent/PH10643A/en unknown
- 1974-09-09 IE IE1870/74A patent/IE40523B1/en unknown
- 1974-09-10 DD DD181015A patent/DD116824A5/xx unknown
- 1974-09-10 LU LU70878A patent/LU70878A1/xx unknown
- 1974-09-10 JP JP49103536A patent/JPS6042238B2/en not_active Expired
- 1974-09-10 FR FR7430568A patent/FR2242984B1/fr not_active Expired
- 1974-09-10 DD DD190238A patent/DD122785A5/xx unknown
- 1974-09-11 NO NO743271A patent/NO140858C/en unknown
- 1974-09-11 BE BE148396A patent/BE819773A/en not_active IP Right Cessation
- 1974-09-11 SU SU7402058406A patent/SU577987A3/en active
- 1974-09-11 GB GB47893/76A patent/GB1484482A/en not_active Expired
- 1974-09-11 ES ES429949A patent/ES429949A1/en not_active Expired
- 1974-09-11 CU CU34115A patent/CU34115A/en unknown
- 1974-09-11 GB GB47894/76A patent/GB1484483A/en not_active Expired
- 1974-09-11 AT AT735174A patent/AT338797B/en not_active IP Right Cessation
- 1974-09-11 HU HUHO1718A patent/HU170427B/hu not_active IP Right Cessation
- 1974-09-11 GB GB39617/74A patent/GB1484481A/en not_active Expired
- 1974-09-12 DE DE2443682A patent/DE2443682C2/en not_active Expired
- 1974-09-12 BR BR7614/74A patent/BR7407614D0/en unknown
-
1975
- 1975-04-25 ES ES437009A patent/ES437009A1/en not_active Expired
- 1975-04-25 ES ES437008A patent/ES437008A1/en not_active Expired
- 1975-04-25 ES ES437013A patent/ES437013A1/en not_active Expired
- 1975-04-25 ES ES437011A patent/ES437011A1/en not_active Expired
- 1975-04-25 ES ES437007A patent/ES437007A1/en not_active Expired
- 1975-04-25 ES ES437012A patent/ES437012A1/en not_active Expired
- 1975-06-20 SU SU752145937A patent/SU609465A3/en active
- 1975-06-20 SU SU7502145932A patent/SU571189A3/en active
- 1975-06-30 AR AR259408A patent/AR211387Q/en unknown
-
1980
- 1980-11-27 YU YU3016/80A patent/YU37154B/en unknown
- 1980-11-27 YU YU3015/80A patent/YU37153B/en unknown
-
1981
- 1981-01-08 HK HK1/81A patent/HK181A/en unknown
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