KR870000349A - 포스폰산 유도체의 제조방법 - Google Patents
포스폰산 유도체의 제조방법 Download PDFInfo
- Publication number
- KR870000349A KR870000349A KR1019860004636A KR860004636A KR870000349A KR 870000349 A KR870000349 A KR 870000349A KR 1019860004636 A KR1019860004636 A KR 1019860004636A KR 860004636 A KR860004636 A KR 860004636A KR 870000349 A KR870000349 A KR 870000349A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogen
- halogen
- compound
- formula
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 8
- 150000003007 phosphonic acid derivatives Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 15
- 239000001257 hydrogen Substances 0.000 claims abstract 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract 12
- 150000002367 halogens Chemical group 0.000 claims abstract 12
- 150000001875 compounds Chemical class 0.000 claims abstract 11
- 150000002431 hydrogen Chemical group 0.000 claims abstract 9
- 125000004970 halomethyl group Chemical group 0.000 claims abstract 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- -1 benzyl halide Chemical class 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Chemical group 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- DOUAWVUJMXAUKO-UHFFFAOYSA-N P(O)(O)=O.NCCC1=CC=CC=C1 Chemical compound P(O)(O)=O.NCCC1=CC=CC=C1 DOUAWVUJMXAUKO-UHFFFAOYSA-N 0.000 claims 1
- 239000002262 Schiff base Substances 0.000 claims 1
- 150000004753 Schiff bases Chemical class 0.000 claims 1
- NMPUDFQLTGMGOH-UHFFFAOYSA-N [1-amino-2-(4-fluorophenyl)ethyl]phosphonic acid Chemical compound OP(=O)(O)C(N)CC1=CC=C(F)C=C1 NMPUDFQLTGMGOH-UHFFFAOYSA-N 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 239000000080 wetting agent Substances 0.000 abstract 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 abstract 2
- 239000002855 microbicide agent Substances 0.000 abstract 2
Classifications
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5333—Arylalkane phosphine oxides or thioxides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/306—Arylalkanephosphinic acids, e.g. Ar-(CH2)n-P(=X)(R)(XH), (X = O,S, Se; n>=1)
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3882—Arylalkanephosphonic acids
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Carbon And Carbon Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- 일반식(II)의 쉬프 염기의 CH2그룹을 활성화시키고, 활성화된 염기를 적절하게 치환된 일반식(III)의 벤질 할라이드로 아르알킬화시킨 다음, 촉매의 존재하에서 일반식(IV)의 중간체를 가수소 분해적으로 분리시키고, R 및/또는 R1이 알콕시일 경우, 임의로 상승된 온도에서 무기산으로 처리하여 히드록실 그룹으로 전환시킴을 특징으로 하여 일반식(I)의 화합물 및 이의 염을 제조하는 방법.상기 식에서,R 및 R1은 각각 서로 독립적으로 C1-C4알킬, C1-C4알콕시 또는 히드록시이며,X는 수소, 할로겐, C1-C4알킬, C1-C4알콕시, 트리메틸실릴, 시아노, 메톡시카보닐 또는 -CH2-CH(NH2) -P(O)(R)(R1)라디칼이고,Y는 수소, 할로겐, C1-C2할로알콕시 또는 C1-C2할로알킬이며,T1은 수소, 또는 지방족이나 방향족 라디칼이고,T2는 지방족 또는 방향족 라디칼이며,Hal은 할로겐 원자이다(단, R 및 R1이 동시에 히드록시 또는 에톡시일 경우, 치환체 X와 Y중에서 적어도 하나는 수소가 아니다).
- 제1항에 있어서, R과 R1이 동시에 히드록시 또는 에톡시이면 치환체 X 또는 Y중의 적어도 하나는 수소가 아닌 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, R=R1=OH이고, X가 수소, 불소, 염소 또는 브롬, C1-C4알킬, CH3O, Si(CH3)3, -CN, -COOCH3또는 -CH2-CH(NH2)-P(O)(OH)2이며, Y는 불소, 염소, 브롬, 할로메톡시 또는 할로메틸인 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, 치환체 X및 Y중에서 적어도 하나가 할로겐이거나 할로겐을 함유하는 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, 치환체 X및 Y중에서 하나가 불소이거나 불소를 함유하는 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, R과 R1이 각각 서로 독립적으로 C1-C4알킬, C1-C4알콕시 또는 히드록시이고, X는 할로겐, C1-C4알킬, C1-C4알콕시, Si (CH3)3시아노 또는 -CH2-CH(NH2)-P(O)(R)(R1)이며, Y는 수소, 할로겐, 할로메톡시, 할로에톡시 또는 할로메틸인 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, R, R1및 Y가 제6항에서 정의한 바와 같고, X는 불소, 염소, 메틸, 에틸, 이소프로필, 3급-부틸, 메톡시, 에톡시, 이소프로폭시 또는 시아노인 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, R 및 R1은 제1항에서 정의한 바와 같고, X는 할로겐, 메틸, 메톡시 또는 시아노이며, Y는 수소, 할로겐, 디플루오로메톡시 또는 트리플루오로메틸인 일반식(I)의 화합물을 제조하는방법.
- 제1항에 있어서, R 및 R1은 제1항에서 정의한 바와 같고, X는 수소이며, Y는 디플루오로 메톡시 또는 트리플루오로메틸인 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, 1-아미노-2-페닐에탄 포스폰산을 제조하는 방법.
- 제1항에 있어서, 1-아미노-2-(4-플로오로페닐)에탄포스폰산을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH246285 | 1985-06-11 | ||
| CH02462/85-0 | 1985-06-11 | ||
| CH2462/85-0 | 1985-06-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR870000349A true KR870000349A (ko) | 1987-02-18 |
| KR940005339B1 KR940005339B1 (ko) | 1994-06-17 |
Family
ID=4234364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860004636A KR940005339B1 (ko) | 1985-06-11 | 1986-06-10 | 포스폰산 유도체의 제조방법 |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP0207890B1 (ko) |
| JP (1) | JPH0753743B2 (ko) |
| KR (1) | KR940005339B1 (ko) |
| AT (1) | ATE50999T1 (ko) |
| AU (1) | AU601153B2 (ko) |
| BR (1) | BR8602695A (ko) |
| CA (1) | CA1313190C (ko) |
| DD (1) | DD251913A5 (ko) |
| DE (1) | DE3669512D1 (ko) |
| DK (1) | DK272886A (ko) |
| ES (1) | ES8800954A1 (ko) |
| GR (1) | GR861496B (ko) |
| IE (1) | IE58475B1 (ko) |
| IL (1) | IL79086A0 (ko) |
| NZ (1) | NZ216484A (ko) |
| PH (1) | PH22874A (ko) |
| PT (1) | PT82737B (ko) |
| ZA (1) | ZA864321B (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5321153A (en) * | 1992-06-15 | 1994-06-14 | Monsanto Company | Process for making chiral alpha-amino phosphonates selected novel chiral alpha-amino phosphonates |
| CA2161114A1 (en) * | 1993-04-23 | 1994-11-10 | Andrew D. Napper | Catalytic antibodies which hydrolyze primary amides and methods for eliciting such antibodies |
| ZA971253B (en) * | 1996-02-16 | 1998-08-14 | Basf Ag | Substituted aromatic phosphonic acid derivatives |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL48835A (en) | 1975-01-27 | 1979-05-31 | Sparamedica Ag | Amino acyl and peptidyl derivatives of phophonic acids, their preparation and pharmaceutical compositions containingthem |
| DE2966111D1 (en) | 1978-10-05 | 1983-10-06 | Ciba Geigy Ag | Process for influencing plant growth |
| US4379146A (en) * | 1981-02-17 | 1983-04-05 | Merck & Co., Inc. | Substituted phosphonamides as antihypertensives |
| EP0103867B1 (en) * | 1982-09-17 | 1986-12-17 | Kyowa Hakko Kogyo Co., Ltd. | Phosphorus-containing peptide derivative |
| CA1258820A (en) * | 1983-03-18 | 1989-08-29 | Hiroshi Asano | Electrolyzing dilute caustic soda solution with sequential polarity inversion |
| SE455259B (sv) * | 1984-01-30 | 1988-07-04 | Kenogard Ab | Anvendning av vissa aminoalkanfosfonsyror for bekempning av svampsjukdomar hos vexter |
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1986
- 1986-06-05 AT AT86810245T patent/ATE50999T1/de not_active IP Right Cessation
- 1986-06-05 DE DE8686810245T patent/DE3669512D1/de not_active Expired - Lifetime
- 1986-06-05 EP EP86810245A patent/EP0207890B1/de not_active Expired - Lifetime
- 1986-06-09 CA CA000511101A patent/CA1313190C/en not_active Expired - Fee Related
- 1986-06-09 PT PT82737A patent/PT82737B/pt not_active IP Right Cessation
- 1986-06-09 PH PH33871A patent/PH22874A/en unknown
- 1986-06-09 DD DD86291125A patent/DD251913A5/de not_active IP Right Cessation
- 1986-06-09 GR GR861496A patent/GR861496B/el unknown
- 1986-06-10 KR KR1019860004636A patent/KR940005339B1/ko active IP Right Grant
- 1986-06-10 DK DK272886A patent/DK272886A/da not_active Application Discontinuation
- 1986-06-10 IE IE154486A patent/IE58475B1/en not_active IP Right Cessation
- 1986-06-10 ZA ZA864321A patent/ZA864321B/xx unknown
- 1986-06-10 ES ES555882A patent/ES8800954A1/es not_active Expired
- 1986-06-10 IL IL79086A patent/IL79086A0/xx not_active IP Right Cessation
- 1986-06-10 NZ NZ216484A patent/NZ216484A/xx unknown
- 1986-06-10 AU AU58509/86A patent/AU601153B2/en not_active Ceased
- 1986-06-10 BR BR8602695A patent/BR8602695A/pt unknown
- 1986-06-11 JP JP61135879A patent/JPH0753743B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| PT82737A (en) | 1986-07-01 |
| JPS61286395A (ja) | 1986-12-16 |
| DE3669512D1 (de) | 1990-04-19 |
| ES555882A0 (es) | 1987-12-01 |
| DK272886A (da) | 1986-12-12 |
| DK272886D0 (da) | 1986-06-10 |
| NZ216484A (en) | 1989-11-28 |
| EP0207890A1 (de) | 1987-01-07 |
| BR8602695A (pt) | 1987-03-17 |
| EP0207890B1 (de) | 1990-03-14 |
| KR940005339B1 (ko) | 1994-06-17 |
| IE861544L (en) | 1986-12-11 |
| AU601153B2 (en) | 1990-09-06 |
| ATE50999T1 (de) | 1990-03-15 |
| PT82737B (pt) | 1988-12-15 |
| IL79086A0 (en) | 1986-09-30 |
| JPH0753743B2 (ja) | 1995-06-07 |
| DD251913A5 (de) | 1987-12-02 |
| PH22874A (en) | 1989-01-19 |
| IE58475B1 (en) | 1993-09-22 |
| CA1313190C (en) | 1993-01-26 |
| ZA864321B (en) | 1987-02-25 |
| AU5850986A (en) | 1986-12-18 |
| ES8800954A1 (es) | 1987-12-01 |
| GR861496B (en) | 1986-10-10 |
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|---|---|---|---|
| A201 | Request for examination | ||
| G160 | Decision to publish patent application | ||
| E701 | Decision to grant or registration of patent right | ||
| NORF | Unpaid initial registration fee |