KR840000546A - 이미다조[1,2-a] 피리딘 및 피라진의 제조방법 - Google Patents
이미다조[1,2-a] 피리딘 및 피라진의 제조방법 Download PDFInfo
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- KR840000546A KR840000546A KR1019820002835A KR820002835A KR840000546A KR 840000546 A KR840000546 A KR 840000546A KR 1019820002835 A KR1019820002835 A KR 1019820002835A KR 820002835 A KR820002835 A KR 820002835A KR 840000546 A KR840000546 A KR 840000546A
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- Prior art keywords
- compound
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- lower alkyl
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- described below
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 title claims 4
- 238000000034 method Methods 0.000 title claims 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 title claims 2
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- -1 —CH 2 CN Chemical group 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 2
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 150000002500 ions Chemical group 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 235000010288 sodium nitrite Nutrition 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 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
- C07D213/60—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 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (45)
- A) 일반식(Ⅱ)의 화합물을 일반식 (Ⅲ)의 화합물과 반응시키거나,
- B) R4가-0-R8-Ar, -0-CH2-CH=CH2, -NH-R8-Ar, -R8-Ar(여기에서 R8과 Ar은 후술할 바와 같음)인 일반식(Ⅰ)의 화합물을 제조하기 위해서는, 일반식(Ⅳ)의 화합물을 일반식(Ⅴ) 화합물과 반응시키거나,
- C) R4가-CH=CH-Ar 또는 -CH=CH-CH2-Ar인 일반식(Ⅰ)의 화합물을 제조하기 위해서는, R2, R3및 R5가 후술하는 바와같고 Z가 CHO인 일반식(Ⅳ)의 화합물을 적당한 위티히 시약과 위티히 반응을 시키거나,
- D) R4가-CH=CH-Ar인 일반식(Ⅰ)의 화합물을 제조하기 위해서는, R2, R3및 R5가 후술하는 바와같고 Z가 포스피닐메틸그룹인 일반식(Ⅳ)의 화합물을 일반식 Ar-CHO(여기에서 Ar은 후술할 바와 같음)인 화합물과 반응시키거나,
- E) R2, R4및 R5가 후술한 바와같고 R3가 CH2CN인 일반식(Ⅰ)의 화합물을 제조하기 위해서는, R3가-CH2X(여기에서 X는 이탈하기 용이한 이탈그룹이)인 일반식(Ⅰ)의 화합물을 금속 시아나이드와 반응시키거나,
- F) R2및 R3중의 적어도 하나가 히드록시저급알킬인 것을 제외하고는 R2, R3, R4및 R5가 후술할 바와같은 일반식(Ⅰ)의 화합물을 제조하기 위해서는, R2및 또는 R3가-(R')nCOOR(여기에서 R'는 탄소수 1내지 5의 저급알킬렌이고 n은 0 또는 1이며 R은 탄화수소 그룹이다)인 일반식(Ⅰ)의 화합물을 환원시키거나,
- G) R2, R4및 R5가 후술할 바와같고 R3가-NO인 일반식(Ⅰ)의 화합물을 제조하기 위해서는, R3가 수소인 일반식(Ⅰ)의 화합물을 3-위치에서 니트로소화하거나,
- H) R2, R4및 R5가 후술할 바와같고 R3가 -NH2인 일반식(Ⅰ)의 화합물을 제조하기 위해서는, R3가 -NO 또는 -NO2인 일반식(Ⅰ)의 화합물을 환원시키거나,
- I) R2, R4및 R5가 후술할 바와같고 R3가 -NR6R7(여기에서 R6및 또는 R7은 저급알킬이다)인 일반식(Ⅰ)의 화합물을 제조하기 위해서는, R3가 -NH2인 일반식(Ⅰ)의 화합물을 알킬화시키거나,
- J) R2, R4및 R5가 후술할 바와같고 R3가 -CH2NC인 일반식(Ⅰ)의 화합물을 제조하기 위해서는, R3가인 일반식(Ⅰ)의 화합물을 아민의 존재하에서 PCl3와 반응시키고, 제조된 일반식(Ⅰ)의 화합물을 필요시 환원시켜 상응하는 2,3-디하이드로-, 5,6,7,8-테트라 하이드로-, 2,3,5,6,7,8-헥사하이드로 유도체를 제조하고, 필요시 그의 염으로 전환시킴을 특징으로 하여 일반식(Ⅰ)의 이미다조[1,2-a]피리딘 및 피라진, 그의 2,3-디하이드로-, 5,6,7,8-테트라하이드로와 2,3,5,6,7,8-헥사하이드로 유도체 및 이러한 화합물들의 약제학적으로 허용할 수 있는 염을 제조하는 방법.
-
- 상기식에서
- B는 CH 또는 N이고
- B가 CH를 나타내면,
- R2는 수소, 저급알킬 또는 히드록시 저급알킬이고
- R5는 수소, 할로겐 또는 저급알킬이며
- R3는 저급알킬, -CH2CN, 히드록시 저급알킬,
- -NO, -CH2NC, 또는이거나
- R2가 수소가 아니면
- R3는 또한 수소이고
- R4는 핵의 5,6 또는 7-위치 중의 어느 위치에도 부착될 수 있으며, -O-R8-Ar, -NH-R8-Ar, -R8-Ar, -CH=CH-Ar, -CH-CH2-Ar 또는 -O-CH2-CH=CH|2이거나,
- R3는 전술된 바와 같고
- R4는 핵의 8-위치에 부착되고, -CH=CH-Ar, -CH=CH-CH2-Ar 또는 -O-CH2-CH=CH|2이거나,
- R3는 -NO, -CH2NC 또는이고
- R4는 핵의 8-위치에 부착되고, -O-R8-Ar, -NH-R8-Ar 또는 -R8-Ar이며
- B가 N이면,
- R5는 전술된 바와 같고
- R2및 R3는 서로 무관하게 수소, 저급알킬,
- 히드록시저급알킬, -CH2CN, -NO 및 -NR6R7이며,
- R4는 -O-R8-Ar, -NH-R8-Ar, -R8-Ar, -CH=CH-Ar 또는 -CH=CH-CH-CH|2-Ar이며
- 상기 정의중에서 R6및 R7은 서로 무관하게 수소 또는 저급 알킬이며, R8은 직쇄 또는 측쇄의 저급알킬렌그룹이며
- Ar은 티에닐, 푸라닐, 피리딜, 페닐 또는 할로겐 및 저급알킬 중에서 선택한 하나 이상의 치환체로 치환된 페닐이며
- Z"는 용이하게 이탈되는 이탈그룹이고
- Hal은 Br, Cl 또는 I 이며
- Z는 할로겐, OH 또는 NH2이고
- Z'는 -R8-Ar 또는 -CH2-CH=CH2이며
- 단, 일반식(Ⅲ)의 화합물에서 R2또는 R3에 존재하는 유리의 아미노 또는 히드록시그룹은 보호그룹으로 보호될 수 있으며 이 보호그룹은 이어서 제거된다.
- 제 1 항에 있는 공정 A)에 있어서, Z"가 할로겐, 토실 또는 메실이고 불활성 용매중에서 반응물을 함께 가열하여 반응시킴이 특징이고,
- 공정 B)에 있어서, Z가 할로겐이면 구리촉매를 사용함이 특징이고,
- 공정 C)에 있어서, 사용된 위티히 시약이 일반식(여기에서 Ar은 제 1 항에서 정의된 바와 같고 R은 탄화수소 그룹이다)임이 특징이고,
- 공정 E)에 있어서, X가 할로겐, 알콕시, 아릴옥시, 메실, 토실, 4급그룹 바람직하게는 N(CH3)3I이거나 4급 이온이 BF4 -, PF6 , CF3SO3 및 FSO3 중에서 선택된 비-친핵성 반대이온인 4급 그룹이며 금속 시아나이드가 알카리 금속 시아나이드 임이 특징이고,
- 공정 F)에 있어서, 리튬 알루미늄 하이드라이드를 사용하여 환원시킴이 특징이고,
- 공정 G)에 있어서, 농염산의 존재하에 아질산염 바람직하게는 아질산 나트륨으로 니트로소화시킴이 특징이고,
- 공정 H)에 있어서, 아세트산 존재하의 아연분말로 환원시킴이 특징인 제 1 항에 따른 제조방법.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US27757681A | 1981-06-26 | 1981-06-26 | |
US277576 | 1981-06-26 | ||
US356052 | 1982-03-08 | ||
US06/356,052 US4507294A (en) | 1982-03-08 | 1982-03-08 | Imidazo[1,2-a]pyrazines |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840000546A true KR840000546A (ko) | 1984-02-25 |
KR880001718B1 KR880001718B1 (ko) | 1988-09-08 |
Family
ID=26958574
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR8202835A KR880001718B1 (ko) | 1981-06-26 | 1982-06-25 | 이미다조[1,2-a] 피리딘 및 피라진의 제조방법 |
Country Status (18)
Country | Link |
---|---|
US (1) | US4450164A (ko) |
EP (1) | EP0068378B1 (ko) |
KR (1) | KR880001718B1 (ko) |
AU (1) | AU556062B2 (ko) |
DE (1) | DE3269604D1 (ko) |
DK (1) | DK284482A (ko) |
ES (1) | ES8307806A1 (ko) |
FI (1) | FI73433C (ko) |
GR (1) | GR74924B (ko) |
HU (1) | HU189595B (ko) |
IE (1) | IE53324B1 (ko) |
IL (1) | IL66141A0 (ko) |
MA (1) | MA19513A1 (ko) |
MY (1) | MY8700624A (ko) |
NO (1) | NO159724C (ko) |
NZ (1) | NZ201066A (ko) |
OA (1) | OA07130A (ko) |
PT (1) | PT75115B (ko) |
Cited By (1)
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KR100490790B1 (ko) * | 1997-08-11 | 2005-09-12 | 주식회사 휴비스 | 모세관냉각장치를이용한단성분중공자발권축섬유의제조방법 |
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GB8305245D0 (en) * | 1983-02-25 | 1983-03-30 | Fujisawa Pharmaceutical Co | Imidazo-heterocyclic compounds |
US4507481A (en) * | 1983-07-29 | 1985-03-26 | Pennwalt Corporation | Pyrrolo[1,2-a]imidazoles and imidazo[1,2-a]pyridines |
US4578387A (en) * | 1984-03-05 | 1986-03-25 | Eli Lilly And Company | Inotropic agents |
GB8415540D0 (en) * | 1984-06-18 | 1984-07-25 | Fujisawa Pharmaceutical Co | Imidazoisoquinoline compounds |
JPS61218589A (ja) * | 1985-03-26 | 1986-09-29 | Eisai Co Ltd | 5―(6―イミダゾ〔1,2―a〕ピリジニル)ピリジン誘導体 |
DE3516458A1 (de) * | 1985-05-08 | 1986-11-13 | W. Schlafhorst & Co, 4050 Mönchengladbach | Angetriebener fadenspeicher |
US4725601A (en) * | 1985-06-04 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Certain imidazo[1,2-a]pyridines useful in the treatment of ulcers |
US4596872A (en) * | 1985-06-05 | 1986-06-24 | Schering A.G. | Imidazo[1,2-a]pyridines, and process for their preparation |
EP0228006A1 (en) * | 1985-12-16 | 1987-07-08 | Fujisawa Pharmaceutical Co., Ltd. | Imidazopyridine compounds and processes for preparation thereof |
US4727145A (en) * | 1986-09-22 | 1988-02-23 | Ortho Pharmaceutical Corporation | 2- Or 3- aryl substituted imidazo [1,2-a]pyridines |
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-
1982
- 1982-06-21 EP EP82105411A patent/EP0068378B1/en not_active Expired
- 1982-06-21 DE DE8282105411T patent/DE3269604D1/de not_active Expired
- 1982-06-24 NZ NZ201066A patent/NZ201066A/en unknown
- 1982-06-24 MA MA19720A patent/MA19513A1/fr unknown
- 1982-06-24 FI FI822266A patent/FI73433C/fi not_active IP Right Cessation
- 1982-06-24 NO NO822128A patent/NO159724C/no unknown
- 1982-06-24 IE IE1515/82A patent/IE53324B1/en not_active IP Right Cessation
- 1982-06-24 PT PT75115A patent/PT75115B/pt not_active IP Right Cessation
- 1982-06-24 GR GR68556A patent/GR74924B/el unknown
- 1982-06-24 OA OA57720A patent/OA07130A/xx unknown
- 1982-06-24 DK DK284482A patent/DK284482A/da not_active Application Discontinuation
- 1982-06-24 AU AU85178/82A patent/AU556062B2/en not_active Ceased
- 1982-06-25 HU HU822071A patent/HU189595B/hu not_active IP Right Cessation
- 1982-06-25 IL IL66141A patent/IL66141A0/xx not_active IP Right Cessation
- 1982-06-25 ES ES513431A patent/ES8307806A1/es not_active Expired
- 1982-06-25 KR KR8202835A patent/KR880001718B1/ko active
- 1982-12-20 US US06/450,885 patent/US4450164A/en not_active Expired - Lifetime
-
1987
- 1987-12-30 MY MY624/87A patent/MY8700624A/xx unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100490790B1 (ko) * | 1997-08-11 | 2005-09-12 | 주식회사 휴비스 | 모세관냉각장치를이용한단성분중공자발권축섬유의제조방법 |
Also Published As
Publication number | Publication date |
---|---|
EP0068378A1 (en) | 1983-01-05 |
MA19513A1 (fr) | 1982-12-31 |
MY8700624A (en) | 1987-12-31 |
NO159724C (no) | 1989-02-01 |
NO822128L (no) | 1982-12-27 |
DE3269604D1 (en) | 1986-04-10 |
FI73433C (fi) | 1987-10-09 |
ES513431A0 (es) | 1983-08-01 |
ES8307806A1 (es) | 1983-08-01 |
GR74924B (ko) | 1984-07-12 |
OA07130A (fr) | 1984-03-31 |
IE821515L (en) | 1982-12-26 |
PT75115B (en) | 1985-06-28 |
NO159724B (no) | 1988-10-24 |
EP0068378B1 (en) | 1986-03-05 |
IE53324B1 (en) | 1988-10-12 |
HU189595B (en) | 1986-07-28 |
PT75115A (en) | 1982-07-01 |
AU556062B2 (en) | 1986-10-23 |
FI73433B (fi) | 1987-06-30 |
IL66141A0 (en) | 1982-09-30 |
KR880001718B1 (ko) | 1988-09-08 |
FI822266L (fi) | 1982-12-27 |
NZ201066A (en) | 1985-08-16 |
FI822266A0 (fi) | 1982-06-24 |
US4450164A (en) | 1984-05-22 |
DK284482A (da) | 1982-12-27 |
AU8517882A (en) | 1983-01-06 |
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