KR890003730A - 1-페닐-3-(1-피페라지닐)-1h-인다졸, 그의 제조방법 및 중간생성물, 및 약제로서의 용도 - Google Patents
1-페닐-3-(1-피페라지닐)-1h-인다졸, 그의 제조방법 및 중간생성물, 및 약제로서의 용도 Download PDFInfo
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- KR890003730A KR890003730A KR1019880010045A KR880010045A KR890003730A KR 890003730 A KR890003730 A KR 890003730A KR 1019880010045 A KR1019880010045 A KR 1019880010045A KR 880010045 A KR880010045 A KR 880010045A KR 890003730 A KR890003730 A KR 890003730A
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- lower alkyl
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- CSXIPFGAQMHZPG-UHFFFAOYSA-N 1-phenyl-3-piperazin-1-ylindazole Chemical compound C1CNCCN1C(C1=CC=CC=C11)=NN1C1=CC=CC=C1 CSXIPFGAQMHZPG-UHFFFAOYSA-N 0.000 title claims 2
- 239000003814 drug Substances 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 16
- 239000002253 acid Substances 0.000 claims 8
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- -1 amino, nitro, cyano, mercapto, hydroxy Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 230000000202 analgesic effect Effects 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 210000001072 colon Anatomy 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- WWOASJPLBVFXQR-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(4-methylpiperazin-1-yl)indazole Chemical compound C1CN(C)CCN1C(C1=CC=CC=C11)=NN1C1=CC=C(F)C=C1 WWOASJPLBVFXQR-UHFFFAOYSA-N 0.000 claims 1
- ADMHWUORXYBEMA-UHFFFAOYSA-N 3-(4-ethylpiperazin-1-yl)-1-[4-(trifluoromethyl)phenyl]indazole Chemical compound C1CN(CC)CCN1C(C1=CC=CC=C11)=NN1C1=CC=C(C(F)(F)F)C=C1 ADMHWUORXYBEMA-UHFFFAOYSA-N 0.000 claims 1
- QJCWPBBJTUYEBK-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)-1-phenylindazole Chemical compound C1CN(C)CCN1C(C1=CC=CC=C11)=NN1C1=CC=CC=C1 QJCWPBBJTUYEBK-UHFFFAOYSA-N 0.000 claims 1
- MGGHRBFIBNRPGL-UHFFFAOYSA-N 3-[4-(dimethylphosphorylmethyl)piperazin-1-yl]-1-phenylindazole Chemical compound C1CN(CP(C)(=O)C)CCN1C(C1=CC=CC=C11)=NN1C1=CC=CC=C1 MGGHRBFIBNRPGL-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 230000001430 anti-depressive effect Effects 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 claims 1
- 229940005513 antidepressants Drugs 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
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- 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
- A61P25/24—Antidepressants
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- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
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- 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
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
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Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 일반식(Ⅰ)의 화합물, 그의 기하 이성체, 광학적 대장체 또는 약제학적으로 허용되는 산부가염.상기식에서, n은 0또는 1의 정수이고; m은 0내지 2의 정수이며; X 및 Y는 독립적으로, 할로겐, 저급알킬, 저급알콕시, 저급알킬티오, 디저급알킬아미노, 저급알킬아미노, 아미노, 니트로, 시아노, 머캡토, 하이드록시 또는 트리플루오로 메틸이고, 각각의 m에 대해 Y는 같거나 다를 수 있으며; R은 수소, 저급알킬, 사이클로알킬 저급알킬, 저급알케닐, 하이드록시 저급알킬, 디저급알킬아미노 저급알킬, 디저급알킬포스피닐 저급알킬, 시아노, 저급알킬카보닐, 저급알카노일, 아미노카보닐, 저급알킬아미노카보닐, 또는 일반식의 그룹(여기서, q는 0 내지 5의 정수이고; X1은 할로겐, 저급알킬, 저급알콕시, 저급알킬티오, 디저급알킬아미노, 저급알킬아미노, 아미노, 니트로, 시아노, 머캡토, 하이드록시, 또는 트리플루오로 메틸이며; P는 0 내지 2의 정수이고; 각각의 P에 대해 X1은 같거나 다를 수 있다)이다.
- 제1항에 있어서, n은 0이고, m이 0 또는 1이며, Y가 할로겐 또는 트리플루오로 메틸이며, R이 수소, 저급알킬, 사이클로알킬 저급알킬, 저급알케닐,저급알카노일, 아미노카보닐, 저급알킬아미노 저급알킬, 디저급알킬아미노 저급알킬 또는 디저급알킬포스피닐 저급알킬인 화합물.
- 제2항에 있어서, R이 수소, 저급알킬, 또는 사이클로알킬 저급알킬인 화합물.
- 제3항에 있어서, 1-페닐-3-(1-피페라지닐)-1H-인다졸, 또는 그의 약제학적으로 허용되는 산부가염.
- 제3항에 있어서, 1-페닐-3-(4-메틸-1-피페라지닐)-1H-인다졸 또는 그의 약제학적으로 허용되는 산부가염.
- 제3항에 있어서, 1-(4-플루오로페닐)-3-(4-메틸-1-피페라지닐)-1H-인다졸 또는 그의 약제학적으로 허용되는 산부가염.
- 제2항에 있어서, 3-[4-(디메틸포스피닐 메틸)-1-피페라지닐]-1-페닐-1H-인다졸 또는 그의 약제학적으로 허용되는 산부가염.
- 제3항에 있어서, 3-(4-에틸-1-피페라지닐)-1-[4-(트리플루오로 메틸)페닐]-1H-인다졸 또는 그의 약제학적으로 허용되는 산부가염.
- 일반식(Ⅱ)의 화합물, 그의 기하 이성체, 광학적 대장체, 또는 약제학적으로 허용되는 산부가염.상기식에서, R은 저급알킬, 저급알콕시카보닐 또는 일반식의 그룹(여기에서, X1은 할로겐, 저급알킬, 저급알콕시, 저급알킬티오, 디저급알킬아미노, 니트로, 시아노, 또는 트리플루오로 메틸이며; P는 0 내지 2의 정수이고, 각각의 P에 대해 X1은 같거나 다를 수 있다)이며; X 및 Y는 독립적으로, 할로겐, 저급알킬, 저급알콕시, 저급알킬티오, 디저급알킬아미노, 니트로, 시아노 또는 트리플루오로 메틸이며; n은 0 또는 1의 정수이며; m는 0 내지 2의 정수이고; 각각의 m에 대해, Y는 같거나 다를 수 있으며; Z는 불소 또는 염소이다.
- 약제학적으로 적절한 담체와 함께 활성성분으로서 제1항에 정의된 화합물을 함유하는 약제학적 조성물.
- 진통, 진경 및/또는 항우울 활성을 가지는 약제를 제조하기 위한, 제1항에 정의된 화합물의 용도.
- a) 일반식(Ⅱ)의 화합물을 불활성 유기용매의 존재하에 무기염기로 처리하고; b) 임의로 R이 저급알콕시카보닐인 일반식(Ⅰ)의 화합물을 가수분해시켜 R이 수소인 일반식(Ⅰ)의 화합물을 제공하고; c) 임의로 R이 수소인 일반식(Ⅰ)의 화합물을 일반식 R1X2의 할라이드(여기에서, R1은 저급알킬, 사이클로알킬저급알킬, 하이드록저급알킬, 저급알케닐, 디저급알킬포스피닐 저급알킬, 디저급알킬아미노, 저급알카노일, 시아노 또는 일반식(여기에서, q,p, 및 X1은 상기 정의된 바와 같다)의 라디칼이며, X2는 할로겐이다)로 처리하여 R이 상기 정의된 R1의 의미를 갖는 일반식(Ⅰ)의 화합물을 제공하고, d) 임의로 R이 수소인 일반식(Ⅰ)의 화합물을 무수 아세트산의 존재하에 포름산으로 처리하여 R이 포르밀 그룹인 일반식(Ⅰ)의 화합물을 제공하고, e) 임의로 R이 수소인 일반식(Ⅰ)의 화합물을 일반식(여기에서, R2는 수소 또는 저급알킬이다)의 니트로-치환된 우레아로 처리하여 R이 아미노카보닐 또는 저급알킬아미노 카보닐인 일반식(Ⅰ)의 화합물을 제공하고, f) 임의로 당분야에 공지된 통상의 방법으로 그의 약제학적으로 허용되는 산부가염을 제조함을 특징으로 하여 제1항에 정의된 화합물을 제조하는 방법.상기식에서, X,Y,m 및 n은 제9항에 정의된 바와같으며, R은 저급알킬, 저급알콕시카보닐 또는 페닐이며, Z는 불소 또는 염소이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8276087A | 1987-08-07 | 1987-08-07 | |
| US082760 | 1987-08-07 |
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| Publication Number | Publication Date |
|---|---|
| KR890003730A true KR890003730A (ko) | 1989-04-17 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1019880010045A KR890003730A (ko) | 1987-08-07 | 1988-08-06 | 1-페닐-3-(1-피페라지닐)-1h-인다졸, 그의 제조방법 및 중간생성물, 및 약제로서의 용도 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0302423A3 (ko) |
| JP (1) | JPS6466171A (ko) |
| KR (1) | KR890003730A (ko) |
| AU (2) | AU607792B2 (ko) |
| DK (1) | DK440488A (ko) |
| FI (1) | FI883646A (ko) |
| IL (1) | IL87361A0 (ko) |
| NO (1) | NO171679C (ko) |
| NZ (1) | NZ225714A (ko) |
| PT (1) | PT88202A (ko) |
| ZA (1) | ZA885766B (ko) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4999356A (en) * | 1987-08-07 | 1991-03-12 | Hoechst-Roussel Pharmaceuticals, Inc. | 1-phenyl-3-(1-piperazinyl)-1H-indazoles |
| NZ230045A (en) | 1988-08-05 | 1990-11-27 | Janssen Pharmaceutica Nv | 3-piperazinylbenzazole derivatives and pharmaceutical compositions |
| US5015740A (en) * | 1988-08-05 | 1991-05-14 | Janssen Pharmaceutica N.V. | Antipsychotic 3-piperazinylbenzazole derivatives |
| US4957916A (en) * | 1988-08-05 | 1990-09-18 | Janssen Pharmaceutica N.V. | Antipsychotic 3-piperazinylbenzazole derivatives |
| US5364866A (en) | 1989-05-19 | 1994-11-15 | Hoechst-Roussel Pharmaceuticals, Inc. | Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics |
| US5561128A (en) * | 1989-05-19 | 1996-10-01 | Hoechst-Roussel Pharmaceuticals, Inc. | N-[(4-(heteroaryl)-1-piperidinyl)alkyl]-10,11-dihydro-5H-dibenz[B,F]azepines and related compounds and their therapeutic utility |
| US5776963A (en) * | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
| US4954503A (en) * | 1989-09-11 | 1990-09-04 | Hoechst-Roussel Pharmaceuticals, Inc. | 3-(1-substituted-4-piperazinyl)-1H-indazoles |
| US5041445A (en) * | 1990-05-21 | 1991-08-20 | Hoechst-Roussel Pharmaceuticals Incorporated | 3-[1-thiazolidinylbutyl-4-piperazinyl]-1H-indazoles |
| NZ243065A (en) * | 1991-06-13 | 1995-07-26 | Lundbeck & Co As H | Piperidine derivatives and pharmaceutical compositions |
| DK55192D0 (da) * | 1992-04-28 | 1992-04-28 | Lundbeck & Co As H | 1-piperazino-1,2-dihydroindenderivater |
| JP3462501B2 (ja) * | 1992-11-23 | 2003-11-05 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | 置換された３−（アミノアルキルアミノ）−１，２−ベンゾイソキサゾールおよび関連化合物 |
| EP0833820B1 (en) * | 1995-06-06 | 2001-02-14 | Aventis Pharmaceuticals Inc. | Benzisoxazole and indazole derivatives as antipsychotic agents |
| IL126745A (en) * | 1997-11-04 | 2003-09-17 | Pfizer Prod Inc | Methods of preparing 4-cyano-4- (substituted indazole) cyclohexanecarboxylic acids useful as pde4 inhibitors |
| JP2014166961A (ja) * | 2011-06-20 | 2014-09-11 | Dainippon Sumitomo Pharma Co Ltd | 新規インダゾール誘導体 |
-
1988
- 1988-07-30 EP EP19880112408 patent/EP0302423A3/en not_active Withdrawn
- 1988-08-04 NO NO883465A patent/NO171679C/no unknown
- 1988-08-04 FI FI883646A patent/FI883646A/fi not_active Application Discontinuation
- 1988-08-05 IL IL87361A patent/IL87361A0/xx unknown
- 1988-08-05 JP JP63194742A patent/JPS6466171A/ja active Pending
- 1988-08-05 DK DK440488A patent/DK440488A/da unknown
- 1988-08-05 NZ NZ225714A patent/NZ225714A/en unknown
- 1988-08-05 PT PT88202A patent/PT88202A/pt unknown
- 1988-08-05 AU AU20434/88A patent/AU607792B2/en not_active Ceased
- 1988-08-05 ZA ZA885766A patent/ZA885766B/xx unknown
- 1988-08-06 KR KR1019880010045A patent/KR890003730A/ko not_active Application Discontinuation
-
1990
- 1990-12-19 AU AU68242/90A patent/AU6824290A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DK440488D0 (da) | 1988-08-05 |
| FI883646A0 (fi) | 1988-08-04 |
| EP0302423A2 (en) | 1989-02-08 |
| EP0302423A3 (en) | 1991-01-09 |
| IL87361A0 (en) | 1989-01-31 |
| JPS6466171A (en) | 1989-03-13 |
| NO171679B (no) | 1993-01-11 |
| AU2043488A (en) | 1989-02-09 |
| NO883465L (no) | 1989-02-08 |
| NO883465D0 (no) | 1988-08-04 |
| AU607792B2 (en) | 1991-03-14 |
| ZA885766B (en) | 1989-07-26 |
| DK440488A (da) | 1989-02-08 |
| FI883646A (fi) | 1989-02-08 |
| NO171679C (no) | 1993-04-21 |
| NZ225714A (en) | 1991-12-23 |
| AU6824290A (en) | 1991-03-14 |
| PT88202A (pt) | 1989-06-30 |
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