FI63939C - Ett nytt foerfarande foer framstaellning av cis-isomeren av n -dimetyl-9-(3-(4-metyl-1-piperazinyl)propyliden)tioxanten -2sulfonamid anvaendbar vid psykoterapi - Google Patents
Ett nytt foerfarande foer framstaellning av cis-isomeren av n -dimetyl-9-(3-(4-metyl-1-piperazinyl)propyliden)tioxanten -2sulfonamid anvaendbar vid psykoterapi Download PDFInfo
- Publication number
- FI63939C FI63939C FI773073A FI773073A FI63939C FI 63939 C FI63939 C FI 63939C FI 773073 A FI773073 A FI 773073A FI 773073 A FI773073 A FI 773073A FI 63939 C FI63939 C FI 63939C
- Authority
- FI
- Finland
- Prior art keywords
- cis
- trans
- isomer
- thiothixene
- solvent
- Prior art date
Links
- -1 3- (4-METHYL-1-PIPERAZINYL) PROPYLIDEN Chemical class 0.000 title claims description 5
- 229940124530 sulfonamide Drugs 0.000 title description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
- 239000002904 solvent Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 17
- 239000002585 base Substances 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 5
- 239000003495 polar organic solvent Substances 0.000 claims description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 4
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 3
- GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 description 39
- 229960005013 tiotixene Drugs 0.000 description 31
- 239000000243 solution Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000001556 precipitation Methods 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- GFBKORZTTCHDGY-UFWORHAWSA-N (9e)-n,n-dimethyl-9-[3-(4-methylpiperazin-1-yl)propylidene]thioxanthene-2-sulfonamide Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C/CCN1CCN(C)CC1 GFBKORZTTCHDGY-UFWORHAWSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 235000011118 potassium hydroxide Nutrition 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- IRDOTPJGMVWQRT-UHFFFAOYSA-N 9h-thioxanthene-2-sulfonamide Chemical compound C1=CC=C2CC3=CC(S(=O)(=O)N)=CC=C3SC2=C1 IRDOTPJGMVWQRT-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000004816 paper chromatography Methods 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 238000001671 psychotherapy Methods 0.000 description 2
- 238000010956 selective crystallization Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 241000420100 Morinda lucida Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical class CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical class [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229960000882 thiothixene hydrochloride Drugs 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/20—Thioxanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73408176 | 1976-10-20 | ||
| US05/734,081 US4107430A (en) | 1976-10-20 | 1976-10-20 | Conversion of trans- to cis-N,N-dimethyl-9-[3-(4-methyl-1-piperazinyl)propylidene]-thioxanthene-2-sulfonamide and recovery of the cis-isomer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773073A FI773073A (fi) | 1978-04-21 |
| FI63939B FI63939B (fi) | 1983-05-31 |
| FI63939C true FI63939C (fi) | 1983-09-12 |
Family
ID=24950235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773073A FI63939C (fi) | 1976-10-20 | 1977-10-17 | Ett nytt foerfarande foer framstaellning av cis-isomeren av n -dimetyl-9-(3-(4-metyl-1-piperazinyl)propyliden)tioxanten -2sulfonamid anvaendbar vid psykoterapi |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US4107430A (fr) |
| JP (1) | JPS5353674A (fr) |
| AR (1) | AR213867A1 (fr) |
| AT (1) | AT360025B (fr) |
| AU (1) | AU499048B2 (fr) |
| BE (1) | BE859907A (fr) |
| BG (1) | BG32852A3 (fr) |
| CA (1) | CA1085399A (fr) |
| CH (1) | CH625519A5 (fr) |
| CS (1) | CS192494B2 (fr) |
| DD (1) | DD133438A5 (fr) |
| DE (1) | DE2746762C3 (fr) |
| DK (1) | DK159314C (fr) |
| ES (1) | ES463343A1 (fr) |
| FI (1) | FI63939C (fr) |
| FR (1) | FR2368485A1 (fr) |
| GB (1) | GB1542004A (fr) |
| GR (1) | GR69786B (fr) |
| HK (1) | HK31081A (fr) |
| HU (1) | HU173644B (fr) |
| IE (1) | IE45715B1 (fr) |
| IL (1) | IL53056A (fr) |
| IN (1) | IN146954B (fr) |
| LU (1) | LU78336A1 (fr) |
| MX (1) | MX4843E (fr) |
| MY (1) | MY8100275A (fr) |
| NL (1) | NL172062C (fr) |
| NO (1) | NO148713C (fr) |
| NZ (1) | NZ185461A (fr) |
| PH (1) | PH13941A (fr) |
| PL (1) | PL106962B1 (fr) |
| PT (1) | PT67171B (fr) |
| RO (1) | RO74135A (fr) |
| SE (1) | SE437828B (fr) |
| SU (1) | SU831078A3 (fr) |
| YU (1) | YU40978B (fr) |
| ZA (1) | ZA776216B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2998303B1 (fr) | 2014-09-17 | 2018-06-13 | B & G Partners, LLC | Derivées de phenothiazine et procédés pour traiter des tumeurs |
| CN107987053B (zh) * | 2017-12-08 | 2023-04-14 | 植恩生物技术股份有限公司 | 一种高纯度z型盐酸氟哌噻吨的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3115502A (en) * | 1959-06-19 | 1963-12-24 | Hoffmann La Roche | Method of isomerizing basically substituted stereoisomeric thioxanthenes |
| NL103196C (fr) * | 1959-06-19 | |||
| US3310553A (en) * | 1962-09-25 | 1967-03-21 | Pfizer & Co C | Alkylated thioxathenesulfonamides |
| US3514449A (en) * | 1967-01-16 | 1970-05-26 | Pfizer & Co C | Process for separating the cis isomer from a mixture of cis and trans n-(3 - (2 - chlorodibenz(b,e)oxepin - 11(6h)-ylidene)-propyl)piperazine |
| US3681346A (en) * | 1969-06-20 | 1972-08-01 | Kefalas As | {60 -isomer of the decanoic acid ester of 10-{8 3,-(4-hydroxyethyl-1-piperazinyl)propylidene{9 -2-trifluoro-methyl thiaxanthene, acid addition salts thereof, method of use and compositions |
| SU540867A1 (ru) * | 1975-06-16 | 1976-12-30 | Предприятие П/Я М-5927 | Способ получени цис- -диметил9-/3-(4-метил-1-пиперазинил)-пропилиден/-тиоксантен-2-сульфонамида |
-
1976
- 1976-10-20 US US05/734,081 patent/US4107430A/en not_active Expired - Lifetime
-
1977
- 1977-04-19 AU AU29690/77A patent/AU499048B2/en not_active Expired
- 1977-09-26 SE SE7710759A patent/SE437828B/sv not_active IP Right Cessation
- 1977-10-03 IN IN286/DEL/77A patent/IN146954B/en unknown
- 1977-10-04 GR GR54504A patent/GR69786B/el unknown
- 1977-10-05 IL IL53056A patent/IL53056A/xx unknown
- 1977-10-07 PH PH20316A patent/PH13941A/en unknown
- 1977-10-10 YU YU2438/77A patent/YU40978B/xx unknown
- 1977-10-13 AT AT732077A patent/AT360025B/de not_active IP Right Cessation
- 1977-10-14 MX MX776482U patent/MX4843E/es unknown
- 1977-10-17 RO RO7791862A patent/RO74135A/fr unknown
- 1977-10-17 JP JP12437277A patent/JPS5353674A/ja active Granted
- 1977-10-17 FI FI773073A patent/FI63939C/fi not_active IP Right Cessation
- 1977-10-18 CH CH1271377A patent/CH625519A5/fr not_active IP Right Cessation
- 1977-10-18 CA CA288,928A patent/CA1085399A/fr not_active Expired
- 1977-10-18 NZ NZ185461A patent/NZ185461A/xx unknown
- 1977-10-18 PT PT67171A patent/PT67171B/pt unknown
- 1977-10-18 LU LU78336A patent/LU78336A1/fr unknown
- 1977-10-18 BG BG037599A patent/BG32852A3/xx unknown
- 1977-10-18 PL PL1977201585A patent/PL106962B1/pl unknown
- 1977-10-18 DE DE2746762A patent/DE2746762C3/de not_active Expired
- 1977-10-19 IE IE2134/77A patent/IE45715B1/en not_active IP Right Cessation
- 1977-10-19 HU HU77PI595A patent/HU173644B/hu unknown
- 1977-10-19 NO NO773588A patent/NO148713C/no unknown
- 1977-10-19 BE BE181889A patent/BE859907A/fr not_active IP Right Cessation
- 1977-10-19 NL NLAANVRAGE7711471,A patent/NL172062C/xx not_active IP Right Cessation
- 1977-10-19 ZA ZA00776216A patent/ZA776216B/xx unknown
- 1977-10-19 SU SU772531950A patent/SU831078A3/ru active
- 1977-10-19 GB GB7743542A patent/GB1542004A/en not_active Expired
- 1977-10-19 CS CS776800A patent/CS192494B2/cs unknown
- 1977-10-19 DK DK465377A patent/DK159314C/da not_active IP Right Cessation
- 1977-10-19 ES ES463343A patent/ES463343A1/es not_active Expired
- 1977-10-19 FR FR7731487A patent/FR2368485A1/fr active Granted
- 1977-10-20 DD DD77201628A patent/DD133438A5/xx unknown
- 1977-10-20 AR AR269655A patent/AR213867A1/es active
-
1981
- 1981-07-02 HK HK310/81A patent/HK31081A/xx not_active IP Right Cessation
- 1981-12-30 MY MY275/81A patent/MY8100275A/xx unknown
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