CS207699B2 - Method of making the noew 2-atyl-1h-perimidine compounds - Google Patents
Method of making the noew 2-atyl-1h-perimidine compounds Download PDFInfo
- Publication number
- CS207699B2 CS207699B2 CS788575A CS857578A CS207699B2 CS 207699 B2 CS207699 B2 CS 207699B2 CS 788575 A CS788575 A CS 788575A CS 857578 A CS857578 A CS 857578A CS 207699 B2 CS207699 B2 CS 207699B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- perimidine
- compounds
- preparation
- formula
- reacted
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003855 acyl compounds Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 14
- -1 m-trifluoromethylphenyl Chemical group 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- UNDUSVBXIVZGOQ-UHFFFAOYSA-N 1h-perimidin-2-amine Chemical class C1=CC(NC(N)=N2)=C3C2=CC=CC3=C1 UNDUSVBXIVZGOQ-UHFFFAOYSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 36
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 229940125721 immunosuppressive agent Drugs 0.000 abstract 1
- 239000003018 immunosuppressive agent Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 210000000952 spleen Anatomy 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 241000700159 Rattus Species 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000028993 immune response Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 206010061218 Inflammation Diseases 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 210000002683 foot Anatomy 0.000 description 5
- 210000000548 hind-foot Anatomy 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 150000005052 perimidines Chemical class 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 230000001629 suppression Effects 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000003743 erythrocyte Anatomy 0.000 description 4
- 210000004989 spleen cell Anatomy 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 241001494479 Pecora Species 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
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- 102000036639 antigens Human genes 0.000 description 3
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- 238000004364 calculation method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
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- 238000002474 experimental method Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VQHBDGIIHYIOAB-UHFFFAOYSA-N 2-(4-methylphenyl)-1h-perimidine Chemical class C1=CC(C)=CC=C1C(N1)=NC2=CC=CC3=CC=CC1=C23 VQHBDGIIHYIOAB-UHFFFAOYSA-N 0.000 description 2
- JLLGZSXMMPKRFI-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]-1h-perimidine;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(C=2NC=3C=CC=C4C=CC=C(C=34)N=2)=C1 JLLGZSXMMPKRFI-UHFFFAOYSA-N 0.000 description 2
- KXLJLJJNISGKPN-UHFFFAOYSA-N 2-phenyl-1h-perimidine Chemical compound C1=CC=CC=C1C(N1)=NC2=CC=CC3=CC=CC1=C23 KXLJLJJNISGKPN-UHFFFAOYSA-N 0.000 description 2
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- 239000004480 active ingredient Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
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- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 206010025135 lupus erythematosus Diseases 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
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
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- 208000011580 syndromic disease Diseases 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JHBWYQRKOUBPCA-UHFFFAOYSA-N 1-(6-methoxy-1,3-benzothiazol-2-yl)-3-phenylurea Chemical compound S1C2=CC(OC)=CC=C2N=C1NC(=O)NC1=CC=CC=C1 JHBWYQRKOUBPCA-UHFFFAOYSA-N 0.000 description 1
- DJDYQGIUDXFEBG-UHFFFAOYSA-N 2-(4-bromophenyl)-1h-perimidine Chemical compound C1=CC(Br)=CC=C1C(N1)=NC2=CC=CC3=CC=CC1=C23 DJDYQGIUDXFEBG-UHFFFAOYSA-N 0.000 description 1
- PYNMVASVFWXKSK-UHFFFAOYSA-N 2-(4-chlorophenyl)-1h-perimidine Chemical compound C1=CC(Cl)=CC=C1C(N1)=NC2=CC=CC3=CC=CC1=C23 PYNMVASVFWXKSK-UHFFFAOYSA-N 0.000 description 1
- KYZVDBPJDCCYMN-UHFFFAOYSA-N 2-(4-chlorophenyl)-2,3-dihydro-1h-perimidine Chemical compound C1=CC(Cl)=CC=C1C(N1)NC2=C3C1=CC=CC3=CC=C2 KYZVDBPJDCCYMN-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
- VPEJMJCUOXHVRM-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]-1h-perimidine;hydrochloride Chemical compound Cl.C1=CC(C(F)(F)F)=CC=C1C(N1)=NC2=CC=CC3=CC=CC1=C23 VPEJMJCUOXHVRM-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- LYJCNWQXQAONLO-UHFFFAOYSA-N 4-(trichloromethoxy)benzoyl chloride Chemical compound ClC(=O)C1=CC=C(OC(Cl)(Cl)Cl)C=C1 LYJCNWQXQAONLO-UHFFFAOYSA-N 0.000 description 1
- UKJWAZZCGZQPTA-UHFFFAOYSA-N 4-(trifluoromethoxy)benzoyl fluoride Chemical compound FC(=O)C1=CC=C(OC(F)(F)F)C=C1 UKJWAZZCGZQPTA-UHFFFAOYSA-N 0.000 description 1
- AQRMQSZDZHOFAD-UHFFFAOYSA-N 4-(trifluoromethyl)benzenecarbothioic s-acid Chemical compound OC(=S)C1=CC=C(C(F)(F)F)C=C1 AQRMQSZDZHOFAD-UHFFFAOYSA-N 0.000 description 1
- OXLNFFBYPUFBCX-UHFFFAOYSA-N 4-(trifluoromethyl)benzenecarbothioyl chloride Chemical class FC(F)(F)C1=CC=C(C(Cl)=S)C=C1 OXLNFFBYPUFBCX-UHFFFAOYSA-N 0.000 description 1
- OXZYBOLWRXENKT-UHFFFAOYSA-N 4-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=C(C(Cl)=O)C=C1 OXZYBOLWRXENKT-UHFFFAOYSA-N 0.000 description 1
- GHICCUXQJBDNRN-UHFFFAOYSA-M 4-iodobenzoate Chemical compound [O-]C(=O)C1=CC=C(I)C=C1 GHICCUXQJBDNRN-UHFFFAOYSA-M 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 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
- CREHACCKBXNWPL-UHFFFAOYSA-N Cl.FC(OC1=CC=C(C=C1)C=1NC=2C=CC=C3C=CC=C(N1)C23)(F)F Chemical compound Cl.FC(OC1=CC=C(C=C1)C=1NC=2C=CC=C3C=CC=C(N1)C23)(F)F CREHACCKBXNWPL-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 101100441092 Danio rerio crlf3 gene Proteins 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-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
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
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- 240000007472 Leucaena leucocephala Species 0.000 description 1
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- 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
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- 235000010443 alginic acid Nutrition 0.000 description 1
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- 208000007502 anemia Diseases 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
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- 230000001363 autoimmune Effects 0.000 description 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
- 229960002170 azathioprine Drugs 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
- 230000004071 biological effect Effects 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 230000003327 cancerostatic effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
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- 206010009887 colitis Diseases 0.000 description 1
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- 239000008121 dextrose Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000003304 gavage Methods 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
- 230000003394 haemopoietic effect Effects 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000003018 immunoassay Methods 0.000 description 1
- 230000016784 immunoglobulin production Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 208000010805 mumps infectious disease Diseases 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 230000003393 splenic effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- 238000002054 transplantation Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- 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
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Transplantation (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS794191A CS207700B2 (cs) | 1977-12-19 | 1979-06-18 | Způsob výroby nových 2-aryl-1H-perimidinových sloučenin |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86173277A | 1977-12-19 | 1977-12-19 | |
| US05/944,434 US4224326A (en) | 1978-09-21 | 1978-09-21 | Immunosuppressive agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS207699B2 true CS207699B2 (en) | 1981-08-31 |
Family
ID=27127642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS788575A CS207699B2 (en) | 1977-12-19 | 1978-12-19 | Method of making the noew 2-atyl-1h-perimidine compounds |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP0002906B1 (ro) |
| JP (1) | JPS5488279A (ro) |
| AR (1) | AR218350A1 (ro) |
| AT (1) | AT367045B (ro) |
| AU (1) | AU522740B2 (ro) |
| CA (1) | CA1079281A (ro) |
| CH (1) | CH636863A5 (ro) |
| CS (1) | CS207699B2 (ro) |
| DD (1) | DD139849A5 (ro) |
| DE (1) | DE2861747D1 (ro) |
| DK (1) | DK144699C (ro) |
| ES (1) | ES476153A1 (ro) |
| FI (1) | FI66360C (ro) |
| FR (1) | FR2411834A1 (ro) |
| GB (1) | GB2010246B (ro) |
| GR (1) | GR70262B (ro) |
| HU (1) | HU178528B (ro) |
| IE (1) | IE47619B1 (ro) |
| IL (1) | IL56211A (ro) |
| IT (1) | IT1101673B (ro) |
| LU (1) | LU80662A1 (ro) |
| MX (1) | MX5563E (ro) |
| NZ (1) | NZ189150A (ro) |
| PL (1) | PL113258B1 (ro) |
| PT (1) | PT68903A (ro) |
| RO (1) | RO72250A (ro) |
| SU (1) | SU984409A3 (ro) |
| YU (1) | YU297678A (ro) |
| ZA (1) | ZA787054B (ro) |
-
1978
- 1978-12-12 AR AR274760A patent/AR218350A1/es active
- 1978-12-12 NZ NZ189150A patent/NZ189150A/xx unknown
- 1978-12-12 AU AU42431/78A patent/AU522740B2/en not_active Expired
- 1978-12-12 JP JP15407178A patent/JPS5488279A/ja active Pending
- 1978-12-12 PT PT68903A patent/PT68903A/pt unknown
- 1978-12-12 FI FI783808A patent/FI66360C/fi not_active IP Right Cessation
- 1978-12-13 FR FR7835084A patent/FR2411834A1/fr active Granted
- 1978-12-13 GB GB7848213A patent/GB2010246B/en not_active Expired
- 1978-12-13 CA CA317,876A patent/CA1079281A/en not_active Expired
- 1978-12-13 DE DE7878300799T patent/DE2861747D1/de not_active Expired
- 1978-12-13 EP EP78300799A patent/EP0002906B1/en not_active Expired
- 1978-12-14 MX MX787596U patent/MX5563E/es unknown
- 1978-12-14 IL IL56211A patent/IL56211A/xx unknown
- 1978-12-15 IT IT30926/78A patent/IT1101673B/it active
- 1978-12-15 LU LU80662A patent/LU80662A1/xx unknown
- 1978-12-18 PL PL1978211890A patent/PL113258B1/pl unknown
- 1978-12-18 SU SU782697059A patent/SU984409A3/ru active
- 1978-12-18 GR GR57920A patent/GR70262B/el unknown
- 1978-12-18 DK DK567578A patent/DK144699C/da not_active IP Right Cessation
- 1978-12-18 ZA ZA787054A patent/ZA787054B/xx unknown
- 1978-12-18 IE IE2487/78A patent/IE47619B1/en unknown
- 1978-12-18 YU YU02976/78A patent/YU297678A/xx unknown
- 1978-12-18 HU HU78EI827A patent/HU178528B/hu unknown
- 1978-12-18 AT AT0904278A patent/AT367045B/de not_active IP Right Cessation
- 1978-12-18 RO RO7895966A patent/RO72250A/ro unknown
- 1978-12-18 CH CH1284178A patent/CH636863A5/fr not_active IP Right Cessation
- 1978-12-19 ES ES476153A patent/ES476153A1/es not_active Expired
- 1978-12-19 CS CS788575A patent/CS207699B2/cs unknown
- 1978-12-19 DD DD78209925A patent/DD139849A5/de unknown
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