KR830007635A - 4-아미노-6,7-디메록시-2-피페라지노퀴나졸린 유도체의 제조방법 - Google Patents
4-아미노-6,7-디메록시-2-피페라지노퀴나졸린 유도체의 제조방법 Download PDFInfo
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- KR830007635A KR830007635A KR1019810005269A KR810005269A KR830007635A KR 830007635 A KR830007635 A KR 830007635A KR 1019810005269 A KR1019810005269 A KR 1019810005269A KR 810005269 A KR810005269 A KR 810005269A KR 830007635 A KR830007635 A KR 830007635A
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- het
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- 238000000034 method Methods 0.000 title claims 4
- APKHJGDGWQDBGM-UHFFFAOYSA-N 6,7-dimethoxy-2-piperazin-1-ylquinazolin-4-amine Chemical class N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N1CCNCC1 APKHJGDGWQDBGM-UHFFFAOYSA-N 0.000 title 1
- -1 C 1 -C 4 alkoxy Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/22—Nitrogen and oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/44—One nitrogen atom with halogen atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
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- Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (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)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- 일반식(a)의 화합물을 일반식 (b)의 화합물과 반응시킨후 Het가 한로로 치환된 화합물은 일반식 R1R2NH의 아민과 반응시켜 Het가 -NR1R2(R|1및 R2는 후술되는 바와 같음)로 치환된 화합물로 임의로 전환시킴을 특징으로 하는 일반식(I)의 화합물 또는 그의 약학적으로 허용되는 산부가염의 제조방법.상기식에서"Het"는 탄소원자중 하나에 의해 피페라진환에 연결된 피리미디닐, 피라지닐, 피리다지닐 또는 트리아지닐 그룹이며 이 그룹은 C1-C2알킬, C1-C4알콕시, 하이드록시, 아릴, 아릴옥시, 아릴에 의해 치환된 C1-C4알킬, 아릴로 치환된 C1-C4알콕시, C1-C4알킬티오, 할로 및 -NR1R2(R1은 수소 또는 C1-C4알킬이며 R2는 수소, C1-C4알킬, C3-C7사이클로알킬, 아릴 또는 아릴로 치환된 C1-C4알킬이거나 R1과 R2는 함께 이들이 결합된 질소원자와 함께 1-피롤리디닐 그룹 또는 O, S 및 N중에서 선택된 또다른 복소원자를 임의로 함유하는 6-원환포화 복소환 그룹을 나타낸다)중에서 선택된 하나 또는 두개의 치환체에 의해 임의로 치환되거나 6,7-디메톡시-1,2,3,4-테트라하이드로 이소퀴놀-2-일 그룹에 의해 임의로 치환되고A가 용이하게 이탈될 수 있는 그룹이고 B는이거나 B가 용이하게 이탈될 수 있는 그룹이고 A는이다.
- 제1항에 있어서, 언급된 용이하게 이탈될 수 있는 그룹이 할로, C1-C4알콕시 또는 C1-C4알킬티오임을 특징으로 하는 방법.
- 제1항 또는 2항에 있어서, "Het"가 제1항에서 정의된 1개 또는 2개의 치환체로 임의 치환된 피리미딘-2-일, 피리미딘-4-일, 1,3,5-트리아진-2-일, 피리다진-3-일, 또는 피라진-2-일 그룹인 화합물을 제조하는 방법.
- 제1항 내지 3항중의 어느 하나에 있어서 언급된 아릴 및 아릴옥시 그룹이 각기 C1-C4알킬, C1-C4알콕시 및 할로중에서 선택된 1개 또는 2개의 치환체로 임의 치환된 페닐 또는 페녹시인 화합물을 제조하는 방법.
- 제1항 내지 4항중의 어느 하나에 있어서, "Het"가 C1-C4알킬, C1-C|4알콕시, 하이드로시, 페닐, 페녹시, C1-C4알킬티오, 할로 및 -NR1R2(이때 R1은 수소 또는 C1-C4알킬이고 R2는 수소, C1-C4알킬, 페닐 또는 C3-C|7사이클로알킬이거나 R1및 R2가 이들이 부착되어 있는 질소원자와 함께 모르폴리노 그룹을 나타냄)중에서 선택된 1개 또는 2개의 치환체로 비치환 또는 치환되거나 언급된 "Het"그룹이 단일한 6,7-디메톡시-1,2,3,4-테트라하이드로 이소퀴놀-2-일 그룹으로 임의 치환된 화합물을 제조하는 방법.
- 제1항 내지 5항중의 어느 하나에 있어서, "Het"가(a) C1-C4알킬, C1-C4알콕시, 하이드록시, 페닐, 페녹시, C1-C4알킬티오, 할로 또는 -NR1R2(이때 R1은 수소 또는 C1-C4알킬이며 R2는 수소, C1-C4알킬, C3-C7사이클로알킬 또는 페닐이거나 R1과 R2는 이들이 결합된 질소원자와 함께 모르폴리노그룹을 나타낸다)중에서 선택된 하나 또는 2개의 치환체에 의해 치환 또는 비치환된 2-또는 4-피리미디닐이거나, 단일 6,7-디메톡시-1,2,3,4-테트라하이드로 이소퀴놀-2-일 그룹에 의해 치환된 2-또는 4-피리미디닐,(b) C1-C4알콕시, 페녹시 및 -NHR2(R2는 수소 또는 C1-C|4알킬이다)중에서 선택된 2개의 치환체에 의해 치환된 1,3,5-트리아진-2-일(c) C1-C4알콕시, 하이드록시, 페닐, 페녹시, 할로 및 -N(C1-C4알킬)|2중에서 선택된 1개의 치환체에 의해 치환 또는 비치환된 3-피리다지닐,(d) 2-피라지닐 중에서 선택되는 화합물을 제조하는 방법.
- 제1항 내지 6항중의 어느 하나에 있어서, "Het"가인 화합물을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8041411 | 1980-12-29 | ||
| GB80.41411 | 1980-12-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830007635A true KR830007635A (ko) | 1983-11-04 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810005269A KR830007635A (ko) | 1980-12-29 | 1981-12-28 | 4-아미노-6,7-디메록시-2-피페라지노퀴나졸린 유도체의 제조방법 |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US4435401A (ko) |
| EP (1) | EP0055583B1 (ko) |
| JP (1) | JPS57181068A (ko) |
| KR (1) | KR830007635A (ko) |
| AR (1) | AR228631A1 (ko) |
| AT (1) | ATE15191T1 (ko) |
| AU (1) | AU529367B2 (ko) |
| CA (1) | CA1165318A (ko) |
| CS (1) | CS236667B2 (ko) |
| DD (1) | DD201901A5 (ko) |
| DE (1) | DE3172089D1 (ko) |
| DK (1) | DK152430C (ko) |
| ES (1) | ES508383A0 (ko) |
| FI (1) | FI70411C (ko) |
| GR (1) | GR76980B (ko) |
| IE (1) | IE52232B1 (ko) |
| IL (1) | IL64665A (ko) |
| NO (1) | NO814454L (ko) |
| PH (1) | PH17079A (ko) |
| PL (2) | PL136268B1 (ko) |
| PT (1) | PT74205B (ko) |
| YU (1) | YU312781A (ko) |
| ZA (1) | ZA818932B (ko) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI70411C (fi) * | 1980-12-29 | 1986-09-19 | Pfizer | Foerfarande foer framstaellning av nya antihypertensiva 4-amino-6,7-dimetoxi-2-piperazinokinazolin derivat |
| DE3114088A1 (de) * | 1981-04-08 | 1982-10-28 | Bayer Ag, 5090 Leverkusen | Wasserloesliche triazinverbindungen, ihre herstellung und ihre verwendung |
| FR2521560A1 (fr) * | 1982-02-17 | 1983-08-19 | Adir | Nouveaux derives de piperazine et d'homopiperazine, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| CH651027A5 (de) * | 1982-11-12 | 1985-08-30 | Sandoz Ag | Heterocyclische verbindungen, ihre herstellung und verwendung. |
| US5001125A (en) | 1984-03-26 | 1991-03-19 | Janssen Pharmaceutica N.V. | Anti-virally active pyridazinamines |
| JPS61140568A (ja) * | 1984-12-14 | 1986-06-27 | Mitsui Petrochem Ind Ltd | キナゾリン誘導体及びそれを有効成分とする血圧降下剤 |
| CA1307786C (en) * | 1984-12-14 | 1992-09-22 | Keiichi Yokoyama | Quinazoline derivatives and antihypertensive preparations containing same as effective components |
| JPS6267077A (ja) * | 1985-09-18 | 1987-03-26 | Mitsui Petrochem Ind Ltd | キナゾリン誘導体及び医薬 |
| AT384218B (de) * | 1985-12-04 | 1987-10-12 | Gerot Pharmazeutika | Verfahren zur herstellung von neuen chinazolin-derivaten |
| US5072564A (en) * | 1988-10-11 | 1991-12-17 | Campana Technology, Inc. | Decorative panel |
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| US3496179A (en) * | 1967-10-11 | 1970-02-17 | Pfizer & Co C | 2-amino-3,4-dihydroquinazolines |
| US3517005A (en) | 1967-10-26 | 1970-06-23 | Pfizer & Co C | Certain 2- and 4-substituted quinazolines |
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-
1981
- 1981-12-17 FI FI814055A patent/FI70411C/fi not_active IP Right Cessation
- 1981-12-22 DE DE8181306025T patent/DE3172089D1/de not_active Expired
- 1981-12-22 DK DK569781A patent/DK152430C/da not_active IP Right Cessation
- 1981-12-22 EP EP81306025A patent/EP0055583B1/en not_active Expired
- 1981-12-22 AT AT81306025T patent/ATE15191T1/de active
- 1981-12-23 CA CA000393109A patent/CA1165318A/en not_active Expired
- 1981-12-23 ZA ZA@@@@00818932A patent/ZA818932B/xx unknown
- 1981-12-23 US US06/333,672 patent/US4435401A/en not_active Expired - Lifetime
- 1981-12-23 IE IE3053/81A patent/IE52232B1/en unknown
- 1981-12-23 AU AU78846/81A patent/AU529367B2/en not_active Ceased
- 1981-12-28 ES ES508383A patent/ES508383A0/es active Granted
- 1981-12-28 IL IL64665A patent/IL64665A/xx unknown
- 1981-12-28 DD DD81236333A patent/DD201901A5/de unknown
- 1981-12-28 AR AR287957A patent/AR228631A1/es active
- 1981-12-28 PT PT74205A patent/PT74205B/pt unknown
- 1981-12-28 JP JP56216057A patent/JPS57181068A/ja active Granted
- 1981-12-28 NO NO814454A patent/NO814454L/no unknown
- 1981-12-28 GR GR66910A patent/GR76980B/el unknown
- 1981-12-28 KR KR1019810005269A patent/KR830007635A/ko unknown
- 1981-12-28 PH PH26680A patent/PH17079A/en unknown
- 1981-12-29 YU YU03127/81A patent/YU312781A/xx unknown
- 1981-12-29 CS CS819946A patent/CS236667B2/cs unknown
- 1981-12-30 PL PL1981234523A patent/PL136268B1/pl unknown
- 1981-12-30 PL PL1981243280A patent/PL136217B1/pl unknown
-
1983
- 1983-08-24 US US06/526,005 patent/US4483859A/en not_active Expired - Lifetime
- 1983-08-24 US US06/525,964 patent/US4483857A/en not_active Expired - Lifetime
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