KR840002368A - 1-치환 2-피리딜 인돌. 그의 n-옥사이드 및 그 염의 제조방법 - Google Patents
1-치환 2-피리딜 인돌. 그의 n-옥사이드 및 그 염의 제조방법 Download PDFInfo
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- KR840002368A KR840002368A KR1019820005232A KR820005232A KR840002368A KR 840002368 A KR840002368 A KR 840002368A KR 1019820005232 A KR1019820005232 A KR 1019820005232A KR 820005232 A KR820005232 A KR 820005232A KR 840002368 A KR840002368 A KR 840002368A
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- Prior art keywords
- pyridyl
- compound
- alkylene
- phenylene
- lower alkyl
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- 150000003839 salts Chemical class 0.000 title claims 12
- -1 1-substituted 2-pyridyl indole Chemical class 0.000 title claims 10
- 150000001204 N-oxides Chemical class 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 1
- DVZWIMDNRJDHDN-UHFFFAOYSA-N 4-[(3-methyl-2-pyridin-3-ylindol-1-yl)methyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C2=CC=CC=C2C(C)=C1C1=CC=CN=C1 DVZWIMDNRJDHDN-UHFFFAOYSA-N 0.000 claims 1
- HMOBHUOHJFOCQK-UHFFFAOYSA-N 4-[2-(3-methyl-2-pyridin-3-ylindol-1-yl)ethoxy]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1OCCN1C2=CC=CC=C2C(C)=C1C1=CC=CN=C1 HMOBHUOHJFOCQK-UHFFFAOYSA-N 0.000 claims 1
- OMUAELKYUGNZPY-UHFFFAOYSA-N 5-(3-methyl-2-pyridin-3-ylindol-1-yl)pentanoic acid Chemical compound OC(=O)CCCCN1C2=CC=CC=C2C(C)=C1C1=CC=CN=C1 OMUAELKYUGNZPY-UHFFFAOYSA-N 0.000 claims 1
- QNBANBGSXPVVSU-UHFFFAOYSA-N 6-[5-(2-carboxyethyl)-3-methyl-2-pyridin-3-ylindol-1-yl]hexanoic acid Chemical compound OC(=O)CCCCCN1C2=CC=C(CCC(O)=O)C=C2C(C)=C1C1=CC=CN=C1 QNBANBGSXPVVSU-UHFFFAOYSA-N 0.000 claims 1
- CVVKIXNPXDBREE-UHFFFAOYSA-N 8-(3-methyl-2-pyridin-3-ylindol-1-yl)octanoic acid Chemical compound OC(=O)CCCCCCCN1C2=CC=CC=C2C(C)=C1C1=CC=CN=C1 CVVKIXNPXDBREE-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- (1) 하기 일반식(Ⅴ)의 화합물을 하기 일반식(Ⅵ)의 반응 작용성 유도체와 축합시키거나; 또는 (2) 하기 일반식(Ⅶ)의 화합물을 폐환시키거나; 또는 (3) 하기 일반식(Ⅷ)의 화합물을 환화시키거나; 또는(4) 하기 일반식(Ⅰa)에 있어서 기 C를 기 B로 전환시키고, 필요한 경우에는 사슬 A를 A의 정의 범위내에서 연장시키거나; 또는 (5) 하기 일반식(Ⅸ)의 화합물을 탈카복실화하고; 필요한 경우에는 상기 각 공정에 있어서 필요치 않은 반응성기를 일시적으로 보호하며; 필요한 경우에는 하기 일반식(Ⅰ)의 생성 화합물를 본 발명에 따른 다른 화합물로 전환 시키고(또는); 필요한 경우에는 생성되는 유리 화합물을 염으로 또는 생성염을 유리 화합물로 또는 유리 화합물을 또 다른 염으로 전환시키며; 필요한 경우에는 수득되는 이성체 또는 라세미체의 혼합물을 단일 이성체 또는 라세미체로 분할하며; 필요한 경우에는 수득되는 단일 라세미체를 광학대장체로 분할시킴을 특징으로 하는 일반식(Ⅰ)의 1－치환 2－피리딜인돌, 그의 N－옥사이드 및 그의 염의 제조방법.상기 식들에 있어서, R1은 수소 또는 저급 알킬을 나타내고; Rr은 피리딜 또는 저급알킬, 카복시, 저급카콕시카보닐 또는 카바모일로 치환된 피리딜을 나타내며; R2및 R3는 각각 독립하여 수소, 저급알킬, 할로겐, 트리플루오로메틸, 하이드록시, 저급알콕시, 카복시저급알킬, 저급알콕시카보닐, 저급알킬, 카복시, 저급알콕시카보닐 또는 저급알킬－(티오, 설피닐 또는 설포닐)을 나타내거나; 또는 R2및 R3는 인접 탄소원자들 상에서 함께 저급알킬렌 디옥시를 나타내며; A는 탄소원자 1 내지 12의 알킬렌, 탄소원자 2 내지 12의 알케닐렌, 탄소원자 2 내지 12의 알키닐렌, 저급알킬렌 페닐렌 저급알킬렌, 저급알킬렌 페닐렌, 페닐렌 저급알킬렌, 페닐렌, 직결합, 저급알킬렌－(티오 또는 옥시)－저급알킬렌, (티오 또는 옥시)－페닐렌, 저급알킬렌－(티오 또는 옥시)－페닐렌, 페닐렌(티오 또는 옥시)－저급알킬렌 또는 페닐렌 저급알케닐렌을 나타내며; B는 카복시, 저급알복시카보닐, 카바모일, 모노－또는 디－저급알킬카바모일, 하이드록시메틸, 하이드록시카바모일, 5－테트라졸릴 또는 포르밀을 나타내며; C는 상기 B와 상이한 기로서 B로 전환 가능한 기를 나타내며; X는 수소, 알카리금속 또는 트리－저급알킬실릴을 나타낸다.
- 제1항에 있어서 R1이 수소 또는 저급 알킬을 나타내고; Ar이 저급알킬기로 임의 치환된 2－, 3－ 도는 4－피리딜을 나타내며; R2가 수소, 저급알킬, 할로겐, 트리플루오로메틸, 하이드록시, 저급알콕시, 저급알킬티오, 카복시저급알킬 또는 저급알콕시카보닐, 저급알킬을나타내며; R3가 수소를 나타내거나; 또는 R2및 R3가 함께 인접 탄소원자들상에서 저급 알킬렌디옥시를 나타내며; A가 탄소원자 1 내지 12의 알킬렌, 페닐렌, 탄소원자 7 내지 10의 저급(알킬렌페닐렌, 알킬렌－티오－페닐렌 또는 알킬렌－옥시－페닐렌) 또는 직결합을 나타내며; B가 카복시, 저급알콕시카보닐, 카바모일, 하이드록시카바모일, 5－테트라졸릴 또는 하이드록시메틸을 나타내는화합물, 그의 N－옥사이드 및 그의 염의 제조방법.
- 제1항에 있어서 하기 일반식(Ⅱ)의 화합물과 그의 염의 제조방법.상기식에서, R1′은 수소 또는 저급 알킬을 나타내고; R2′ 및 R3′는 서로 독립하여 수소, 저급알킬, 할로겐, 트리플루오로메틸, 하이드록시, 저급알킬티오 또는 저급알콕시를 나타내거나; 또는 R2′ 및 R3′는 함께 인접 탄소원자들상에서 메틸렌디옥시를 나타내며; Pyr는 2－, 3－ 또는 4－피리딜을 나타내며; m는 1 내지 13의 정수를 나타내며; R4는 하이드록시, 저급알콕시 또는 아미노를 나타낸다.
- 제1항에 있어서 하기 일반식(Ⅲ)의 화합물과 그의 염의 제조방법.상기식에서, n는 3 내지 10의 정수이고; P는 0 내지 4의 정수이며; Pyr은 2－, 3－ 또는 4－피리딜이며; R5및 R5는 서로 독립하여 하이드록시 또는 저급 알콕시를 나타낸다.
- 제1항에 있어서 하기 일반식(Ⅳ)의 화합물과 그의 제조방법.상기 식에서 R2′ 및 R3′는 서로 독립하여 수소, 저급알킬, 할로겐, 저급알콕시, 저급알킬티오 또는 하이드록시를 나타내거나; 또는 R2′ 및 R3′는 함께 인접 탄소원자들상에서 메틸렌디옥시를 나타내며; x는 산소, 황 또는 직결합을 나타내며; q는 1 내지 4의 정수이며; R7은 하이드록시 또는 저급알콕시를 나타내며; Pyr은 2－, 3－ 또는 4－피리딜을 나타낸다.
- 제1항에 있어서 1－(5－카복시펜틸)－3－메틸－5－(2－카복시에틸)－2－(3－피리딜)－인돌, 1－[2－(4－카복시펜틸티오)－에틸]－3－메틸－2－(3－피리딜)－인돌, 1－[2－(4카복시페녹시)－에틸]－3－메틸－2－(3－피리딜)－인돌, 1－(4－카복시벤질)－3－메틸－2－(3－피리딜)－인돌 또는 그들의 염의 제조방법.
- 제1항에 있어서 1－(7－카복시헵틸)－3－메틸－2－(3－피리딜)－인돌 또는 그의 염의 제조방법.
- 제1항에 있어서 1－(4－카복시부틸)－3－메틸－2－(3－피리딜)－인돌 또는 그의 염의 제조방법.
- 제1항에 있어서 1－(5－카복시펜틸(－5－클로로－3－메틸－2－(3－피리딜)－인돌 또는 그의 염의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32301881A | 1981-11-19 | 1981-11-19 | |
| US323,018 | 1981-11-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840002368A true KR840002368A (ko) | 1984-06-25 |
| KR880002010B1 KR880002010B1 (ko) | 1988-10-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8205232A KR880002010B1 (ko) | 1981-11-19 | 1982-11-19 | 1-치환 2-피리딜 인돌, 그의 n-옥사이드 및 그의 염의 제조방법 |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0080154B1 (ko) |
| JP (1) | JPS5892677A (ko) |
| KR (1) | KR880002010B1 (ko) |
| AR (3) | AR241428A1 (ko) |
| AT (1) | ATE15196T1 (ko) |
| AU (1) | AU564233B2 (ko) |
| CA (1) | CA1197249A (ko) |
| DD (1) | DD204924A5 (ko) |
| DE (1) | DE3265892D1 (ko) |
| DK (1) | DK169104B1 (ko) |
| ES (4) | ES8501755A1 (ko) |
| FI (1) | FI75344C (ko) |
| GB (1) | GB2111050B (ko) |
| GR (1) | GR77035B (ko) |
| HU (1) | HU190425B (ko) |
| IE (1) | IE54156B1 (ko) |
| IL (1) | IL67284A (ko) |
| NO (1) | NO159929C (ko) |
| NZ (1) | NZ202551A (ko) |
| PH (1) | PH19212A (ko) |
| PT (1) | PT75870B (ko) |
| ZA (1) | ZA828505B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4511573A (en) * | 1983-05-17 | 1985-04-16 | Ciba-Geigy Corporation | 3-Substituted-2-(heteroaryl) indoles |
| GB8524157D0 (en) * | 1984-10-19 | 1985-11-06 | Ici America Inc | Heterocyclic amides |
| US4675332A (en) * | 1984-12-10 | 1987-06-23 | Warner-Lambert Company | Acidic tetrazolyl substituted indole compounds and their use as antiallergy agents |
| US4609733A (en) * | 1984-12-27 | 1986-09-02 | Ciba-Geigy Corporation | 3-keto-substituted-N-pyridylindoles |
| GB8626297D0 (en) * | 1986-11-04 | 1986-12-03 | Ici Plc | Pharmaceutical compositions |
| GB8626296D0 (en) * | 1986-11-04 | 1986-12-03 | Ici Plc | Therapeutic agents |
| GB9319100D0 (en) * | 1993-09-15 | 1993-11-03 | Pfizer Ltd | 3-(3-pyridinyl)h-indoles |
| CA2140722A1 (en) * | 1994-01-24 | 1995-07-25 | Joseph A. Jakubowski | Beta-carboline thromboxane synthase inhibitors |
| US6828344B1 (en) * | 1998-02-25 | 2004-12-07 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| GB0307891D0 (en) * | 2003-04-04 | 2003-05-14 | Angeletti P Ist Richerche Bio | Chemical compounds,compositions and uses |
| AR072297A1 (es) * | 2008-06-27 | 2010-08-18 | Novartis Ag | Derivados de indol-2-il-piridin-3-ilo, composicion farmaceutica que los comprende y su uso en medicamentos para el tratamiento de enfermedades mediadas por la sintasa aldosterona. |
| CN111527080B (zh) * | 2017-12-15 | 2023-09-22 | 百时美施贵宝公司 | 取代的吲哚醚化合物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3468894A (en) * | 1966-11-29 | 1969-09-23 | Geigy Chem Corp | Certain 2-pyridyl-substituted indole derivatives |
| DE2909779A1 (de) * | 1979-03-13 | 1980-09-18 | Thomae Gmbh Dr K | Neue indolderivate, deren herstellung und deren verwendung als arzneimittel |
-
1982
- 1982-11-12 GB GB08232457A patent/GB2111050B/en not_active Expired
- 1982-11-16 DE DE8282110582T patent/DE3265892D1/de not_active Expired
- 1982-11-16 EP EP82110582A patent/EP0080154B1/de not_active Expired
- 1982-11-16 AT AT82110582T patent/ATE15196T1/de active
- 1982-11-17 DD DD82244959A patent/DD204924A5/de not_active IP Right Cessation
- 1982-11-17 ES ES517439A patent/ES8501755A1/es not_active Expired
- 1982-11-17 GR GR69837A patent/GR77035B/el unknown
- 1982-11-17 IL IL67284A patent/IL67284A/xx not_active IP Right Cessation
- 1982-11-17 CA CA000415716A patent/CA1197249A/en not_active Expired
- 1982-11-17 FI FI823938A patent/FI75344C/fi not_active IP Right Cessation
- 1982-11-17 PH PH28151A patent/PH19212A/en unknown
- 1982-11-18 NO NO823869A patent/NO159929C/no unknown
- 1982-11-18 IE IE2749/82A patent/IE54156B1/en not_active IP Right Cessation
- 1982-11-18 DK DK514182A patent/DK169104B1/da not_active IP Right Cessation
- 1982-11-18 PT PT75870A patent/PT75870B/pt not_active IP Right Cessation
- 1982-11-18 AU AU90675/82A patent/AU564233B2/en not_active Ceased
- 1982-11-18 HU HU823704A patent/HU190425B/hu not_active IP Right Cessation
- 1982-11-18 NZ NZ202551A patent/NZ202551A/xx unknown
- 1982-11-18 ZA ZA828505A patent/ZA828505B/xx unknown
- 1982-11-19 KR KR8205232A patent/KR880002010B1/ko not_active IP Right Cessation
- 1982-11-19 AR AR82291366A patent/AR241428A1/es active
- 1982-11-19 JP JP57203514A patent/JPS5892677A/ja active Granted
-
1984
- 1984-02-28 ES ES530126A patent/ES530126A0/es active Granted
- 1984-02-28 ES ES530127A patent/ES8608508A1/es not_active Expired
- 1984-02-28 ES ES530128A patent/ES530128A0/es active Granted
- 1984-11-07 AR AR84298532A patent/AR243519A1/es active
- 1984-11-07 AR AR84298531A patent/AR243177A1/es active
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