NO135590B - - Google Patents
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- Publication number
- NO135590B NO135590B NO1147/72A NO114772A NO135590B NO 135590 B NO135590 B NO 135590B NO 1147/72 A NO1147/72 A NO 1147/72A NO 114772 A NO114772 A NO 114772A NO 135590 B NO135590 B NO 135590B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- tyramine
- pyridyl
- effect
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 28
- 239000000126 substance Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 210000004556 brain Anatomy 0.000 description 14
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 13
- 229960002748 norepinephrine Drugs 0.000 description 13
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 13
- 230000001430 anti-depressive effect Effects 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XWLXNPMITZDCHL-UHFFFAOYSA-N 5-(2-aminopropyl)-2-methylphenol Chemical compound CC(N)CC1=CC=C(C)C(O)=C1 XWLXNPMITZDCHL-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZPDWHORJHVKVPL-UHFFFAOYSA-N 5-(2-aminobutyl)-2-methylphenol Chemical compound CCC(N)CC1=CC=C(C)C(O)=C1 ZPDWHORJHVKVPL-UHFFFAOYSA-N 0.000 description 5
- 208000019901 Anxiety disease Diseases 0.000 description 5
- 239000000935 antidepressant agent Substances 0.000 description 5
- 229940005513 antidepressants Drugs 0.000 description 5
- 230000036506 anxiety Effects 0.000 description 5
- 206010003119 arrhythmia Diseases 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 230000001939 inductive effect Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 description 4
- 229960003914 desipramine Drugs 0.000 description 4
- 229960001158 nortriptyline Drugs 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 239000013558 reference substance Substances 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 208000003663 ventricular fibrillation Diseases 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- -1 H^PO^ Chemical compound 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 2
- 229960000836 amitriptyline Drugs 0.000 description 2
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 230000003126 arrythmogenic effect Effects 0.000 description 2
- ZDIGNSYAACHWNL-UHFFFAOYSA-N brompheniramine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Br)C=C1 ZDIGNSYAACHWNL-UHFFFAOYSA-N 0.000 description 2
- 229960000725 brompheniramine Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 2
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- AXEZWCUFXPGSSA-UHFFFAOYSA-N 3,3-diphenylprop-2-en-1-amine Chemical class C=1C=CC=CC=1C(=CCN)C1=CC=CC=C1 AXEZWCUFXPGSSA-UHFFFAOYSA-N 0.000 description 1
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-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
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- JDOZOOBCADNBIJ-UHFFFAOYSA-N lithium;2h-pyridin-2-ide Chemical compound [Li+].C1=CC=N[C-]=C1 JDOZOOBCADNBIJ-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000002746 orthostatic effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 239000001120 potassium sulphate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000003578 releasing effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE05496/71A SE361663B (zh) | 1971-04-28 | 1971-04-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135590B true NO135590B (zh) | 1977-01-17 |
| NO135590C NO135590C (zh) | 1977-04-27 |
Family
ID=20266610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1147/72A NO135590C (zh) | 1971-04-28 | 1972-04-05 |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5512424B1 (zh) |
| AT (1) | AT319242B (zh) |
| AU (1) | AU469519B2 (zh) |
| BE (1) | BE781105A (zh) |
| BR (1) | BR7202598D0 (zh) |
| CA (1) | CA974999A (zh) |
| CH (1) | CH577474A5 (zh) |
| CY (1) | CY876A (zh) |
| DE (1) | DE2220333C3 (zh) |
| DK (1) | DK138987B (zh) |
| ES (1) | ES401908A1 (zh) |
| FI (1) | FI56378C (zh) |
| FR (1) | FR2134379B1 (zh) |
| GB (1) | GB1366241A (zh) |
| HK (1) | HK69576A (zh) |
| IE (1) | IE36330B1 (zh) |
| IT (1) | IT1188904B (zh) |
| NL (1) | NL170731C (zh) |
| NO (1) | NO135590C (zh) |
| SE (1) | SE361663B (zh) |
| SU (1) | SU422146A3 (zh) |
| ZA (1) | ZA721503B (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE409706B (sv) * | 1976-05-21 | 1979-09-03 | Astra Pharma Prod | Forfarande for framstellning av n,n-dimetyl-3-(4-bromfenyl)-3-3(3-pyridyl)-allylamin dihydroklorid monohydrat |
| SE7909514L (sv) | 1979-11-16 | 1981-05-17 | Astra Laekemedel Ab | Nya halofenyl-pyridyl-allylaminderivat |
| ZA885824B (en) * | 1987-08-14 | 1989-04-26 | Merrell Dow Pharma | Novel antidepressants |
| US5585388A (en) * | 1995-04-07 | 1996-12-17 | Sibia Neurosciences, Inc. | Substituted pyridines useful as modulators of acetylcholine receptors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2712020A (en) * | 1948-07-20 | 1955-06-28 | Burroughs Wellcome Co | Heterocyclic allylamines |
-
1971
- 1971-04-28 SE SE05496/71A patent/SE361663B/xx unknown
-
1972
- 1972-03-06 ZA ZA721503A patent/ZA721503B/xx unknown
- 1972-03-23 BE BE781105A patent/BE781105A/xx not_active IP Right Cessation
- 1972-03-28 FI FI858/72A patent/FI56378C/fi active
- 1972-04-05 NO NO1147/72A patent/NO135590C/no unknown
- 1972-04-10 AU AU40965/72A patent/AU469519B2/en not_active Expired
- 1972-04-12 FR FR7212835A patent/FR2134379B1/fr not_active Expired
- 1972-04-19 ES ES401908A patent/ES401908A1/es not_active Expired
- 1972-04-21 CH CH593872A patent/CH577474A5/xx not_active IP Right Cessation
- 1972-04-24 SU SU1777511A patent/SU422146A3/ru active
- 1972-04-24 AT AT357372A patent/AT319242B/de not_active IP Right Cessation
- 1972-04-26 DE DE2220333A patent/DE2220333C3/de not_active Expired
- 1972-04-26 DK DK205772AA patent/DK138987B/da unknown
- 1972-04-27 BR BR2598/72A patent/BR7202598D0/pt unknown
- 1972-04-27 IE IE555/72A patent/IE36330B1/xx unknown
- 1972-04-27 CA CA140,717A patent/CA974999A/en not_active Expired
- 1972-04-27 GB GB1958872A patent/GB1366241A/en not_active Expired
- 1972-04-27 CY CY876A patent/CY876A/xx unknown
- 1972-04-28 NL NLAANVRAGE7205850,A patent/NL170731C/xx not_active IP Right Cessation
- 1972-04-28 JP JP4602272A patent/JPS5512424B1/ja active Pending
-
1976
- 1976-11-04 HK HK695/76*UA patent/HK69576A/xx unknown
-
1980
- 1980-02-15 IT IT47915/80A patent/IT1188904B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GB1366241A (en) | 1974-09-11 |
| CY876A (en) | 1977-03-18 |
| SE361663B (zh) | 1973-11-12 |
| ZA721503B (en) | 1972-11-29 |
| FR2134379B1 (zh) | 1976-09-17 |
| CA974999A (en) | 1975-09-23 |
| IT8047915A1 (it) | 1981-08-15 |
| AU469519B2 (en) | 1972-10-18 |
| FI56378C (fi) | 1980-01-10 |
| DK138987C (zh) | 1979-05-14 |
| NO135590C (zh) | 1977-04-27 |
| NL170731C (nl) | 1982-12-16 |
| AU4096572A (en) | 1972-10-18 |
| DK138987B (da) | 1978-11-27 |
| CH577474A5 (zh) | 1976-07-15 |
| AT319242B (de) | 1974-12-10 |
| FR2134379A1 (zh) | 1972-12-08 |
| IT1188904B (it) | 1988-01-28 |
| BR7202598D0 (pt) | 1973-07-17 |
| DE2220333B2 (de) | 1979-03-01 |
| DE2220333A1 (de) | 1974-01-31 |
| ES401908A1 (es) | 1975-03-16 |
| BE781105A (fr) | 1972-07-17 |
| SU422146A3 (zh) | 1974-03-30 |
| DE2220333C3 (de) | 1979-11-22 |
| NL7205850A (zh) | 1972-10-31 |
| NL170731B (nl) | 1982-07-16 |
| FI56378B (fi) | 1979-09-28 |
| JPS5512424B1 (zh) | 1980-04-02 |
| IE36330B1 (en) | 1976-10-13 |
| IE36330L (en) | 1972-10-28 |
| IT8047915A0 (it) | 1980-02-15 |
| HK69576A (en) | 1976-11-12 |
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