KR840002354A - 시스, 엔도-2-아자비사이클로-[3.3.0]-옥탄-3-카복실산 유도체의 제조방법 - Google Patents
시스, 엔도-2-아자비사이클로-[3.3.0]-옥탄-3-카복실산 유도체의 제조방법 Download PDFInfo
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- KR840002354A KR840002354A KR1019820004953A KR820004953A KR840002354A KR 840002354 A KR840002354 A KR 840002354A KR 1019820004953 A KR1019820004953 A KR 1019820004953A KR 820004953 A KR820004953 A KR 820004953A KR 840002354 A KR840002354 A KR 840002354A
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- KR
- South Korea
- Prior art keywords
- hydrogen
- compound
- carbon atoms
- formula
- general formula
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- -1 nitro, amino Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 230000002378 acidificating effect Effects 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 235000008206 alpha-amino acids Nutrition 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000006502 nitrobenzyl group Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- YCIPHHOEXQJHNT-UHFFFAOYSA-N 3-oxoprop-2-enoic acid Chemical compound OC(=O)C=C=O YCIPHHOEXQJHNT-UHFFFAOYSA-N 0.000 claims 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- 다음 일반식(Ⅱ)의 화합물을 다음 일반식(Ⅲa) 또는 (Ⅲb)의 화합물과 반응시킨후 생성물을 수소첨가시키거나 또는 산 또는 염기로 처리함을 특징으로 하는, 다음 일반식(Ⅰ)의 화합물 및 이의 생리적으로 허용되는 염의 제조방법.상기식에서, 1 및 5번 브리지-헤드 탄소원자상의 수소원자는 서로에 대해 시스-배위이며 3번 탄소 원자상의 카복실그룹은 2환성 환계에 대해 엔도-위치로 배향하고, R1은 수소, 알릴, 비닐 또는 보호된 천연 α-아미노산 R1-CH(NH2)-COOH의 측쇄이며, R2는 수소, (탄소수 1내지 6의)-알킬, (탄소수 2내지 6의)알케일 또는 아릴-(탄소수 1내지 4의)-알킬이고(단 일반식(Ⅱ)에서는 수소를 제외한다).Y는 수소 또는 하이드록실이며, Z는 수소이거나, 또는 Y 및 Z는 함께 산소이고, X는(탄소수 1내지 6의)-알킬, (탄소수 2내지 6의)-알케닐 또는(탄소수 5내지 9의)-사이클로알킬, 또는(탄소수 1내지 4의)-알킬, (탄소수 1내지 4의)-알콕시, 하이드록실, 할로겐, 니트로, 아미노, (탄소수 1내지 4의)-알킬아미노, 디-(탄소수 1내지 4의(-알킬아미노 또는 메틸렌디옥시로 모노-, 디-또는 트리-치환된(탄소수 6내지 12)의-아릴 또는 인돌-3-일이며, W는 카복실-에스네르화그룹이다.
- 다음 일반식(Ⅵ)의 엔아민 또는 다음 일반식(Ⅶ)의 기를 다음 일반식(Ⅷ)의 N-아실화된 β-할로게노-α-아미노-카복실산 에스테르 또는 다음 일반식(Ⅸ)의 아크릴산 에스테르와 반응시켜 다음 일반식(Ⅹ)의 화합물을 생성시킨후, 이 화합물을 강산의 첨가, 아실 아미드 및 에스테르 분비로써 폐환하여 다음 일반식(XIa) 또는 (IXb)의 화합물을 생성시키고, 이화합물을 전이 금속 촉매 존재하에 촉매적 수소첨가로써 또는 저급 알콜중 보란-아민 착화합물 또는 착붕소 수소화물로 환원시킴으로써 W가 수소인 다음 일반식(Ⅲa) 또는 (Ⅲb)의 화합물로 전환시키며, 임의로 이생성물을 에스테르화하여 W가 탄소수 1내지 6의 알킬 또는 탄소수 7내지 8의 아르알킬인 다음 일반식(Ⅲa) 또는(Ⅲb)의 화합물을 생성시킴을 특징으로 하는, 다음 일반식(Ⅲa) 또는 (Ⅲb)의 화합물 및 이의 산(W가 수소인 경우) 또는 염기와의 염의 제조방법.상기 일반식(Ⅲa) 도는 (Ⅲb)에서 W는 수소, 탄소수 1내지 6의 알킬 또는 탄소수 7내지 8의 아르알킬이며, 상기 일반식(Ⅵ)에서, X1은 탄소수 2내지 10의 디알킬아미노이고, 상기 일반식(Ⅶ)에서 m 및 0은 1내지 3의 정수이며, m 및 0의 총합은 3이상이고, A는 CH2, NH, O 또는 S이며,상기 일반식(Ⅷ)에서, X2는 뉴클레오퓨직 그룹이고, Y1은 탄소수 1내지 5의 알카노일, 탄소수 7내지 9의 아르오일 또는 펩타이드 화학에서 통상적이고 산조건하에서 분리되는 기타 보호그룹이며, R2는 탄소수 1내지 5의 알킬 또는 탄소수 7내지 9의 아르알킬이고, 상기 일반식(Ⅸ)에서 Y1및 R2는 전술한 바와 같으며, 상기 일반식(Ⅹ)에서 R2및 Y1은 전술한 바와 같다.
- a) X가 아릴이면, 아릴메틸 케톤 X-CO-CH3을 글리옥실산 에스테르 CHO-CO2R2및 α-아미노산 에스데르 H2N-CHR1-CO2W(여기서 W′는 염기성 또는 산성 가수분해로써 분리되는 기이고, 만일 W′가 벤질이면 R2는 벤질 또는 니트로벤질이 아니다)와 반응시켜 다음 일반식(Ⅳ)의 화합물을 생성시키거나, 또는 b) 케토-아크릴산 에스테르 X-CO_CH=CH=CO2R2를 α-아미노산 에스테르 H2N-CHCR1)-CO2W′와 반응시켜 다음 일반식(Ⅳ)의 화합물을 생성시키고, 적절하다면 a) 또는 b)에 따라 수득한 이화합물을, W′가 산성 또는 염기성 조건하에서 제거될수 있는 기이면, 산성 또는 염기성 에스테르 분리시키거나, 또는 W′가 벤질 또는 니트로벤질이면(R2=벤질 또는 니트로벤질)이화합물을 가수소분해로써 카복실산으로 전환시키고 이 생성물을 수소첨가시켜 X,R1및 R2가 전술한 바와같고 Y가 수소 또는 하이드록실이며 Z가 수소인, 다음 일반식(Ⅱ)의 화합물 또는 적절하다면 산-촉매적으로 에스테르 분리시키는 이의 저급알킬 에스테르를 생성시킴을 특징으로 하는, 다음 일반식(Ⅱ)의 화합물의 제조방법.상기식에서, x,R1,R2및 W′는 전술한 바와같고, Y는 수소 또는 하이드록실이며, Z는 수소이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3143946 | 1981-11-05 | ||
DE3143946.2 | 1981-11-05 | ||
DEP3143946.2 | 1981-11-05 | ||
DEP3226768.1 | 1982-07-17 | ||
DE19823226768 DE3226768A1 (de) | 1981-11-05 | 1982-07-17 | Derivate der cis, endo-2-azabicyclo-(3.3.0)-octan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840002354A true KR840002354A (ko) | 1984-06-25 |
KR890000007B1 KR890000007B1 (ko) | 1989-03-02 |
Family
ID=25797115
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR8204953A KR890000007B1 (ko) | 1981-11-05 | 1982-11-03 | 시스, 엔도-2-아자비사이클로-[3.3.0]-옥탄-3-카복실산 유도체의 제조방법 |
Country Status (31)
Country | Link |
---|---|
US (4) | US4727160A (ko) |
EP (2) | EP0079022B1 (ko) |
JP (3) | JPH02104573A (ko) |
KR (1) | KR890000007B1 (ko) |
AR (1) | AR240675A1 (ko) |
AU (3) | AU565200B2 (ko) |
BG (1) | BG60532B2 (ko) |
CA (1) | CA1187087A (ko) |
CS (1) | CS247159B2 (ko) |
CZ (1) | CZ416291A3 (ko) |
DD (2) | DD203047A5 (ko) |
DE (3) | DE3226768A1 (ko) |
DK (2) | DK166624C (ko) |
DZ (1) | DZ473A1 (ko) |
ES (3) | ES517066A0 (ko) |
FI (1) | FI81087C (ko) |
GR (1) | GR77381B (ko) |
HK (1) | HK74889A (ko) |
HU (2) | HU186339B (ko) |
IE (1) | IE56476B1 (ko) |
IL (1) | IL67172A (ko) |
JO (1) | JO1224B1 (ko) |
LU (1) | LU88260I2 (ko) |
MA (1) | MA19639A1 (ko) |
NL (1) | NL930039I2 (ko) |
NO (2) | NO156940C (ko) |
NZ (1) | NZ202378A (ko) |
PH (2) | PH22417A (ko) |
PT (1) | PT75792A (ko) |
SG (1) | SG1189G (ko) |
SU (1) | SU1277895A3 (ko) |
Cited By (1)
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US11289233B2 (en) | 2016-04-28 | 2022-03-29 | Kepco Nuclear Fuel Co., Ltd. | Method for collecting uranium by treatment process of washing waste liquid generated in uranium hexafluoride cylinder washing process |
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DE3174844D1 (en) * | 1980-10-23 | 1986-07-24 | Schering Corp | Carboxyalkyl dipeptides, processes for their production and pharmaceutical compositions containing them |
DE3226768A1 (de) * | 1981-11-05 | 1983-05-26 | Hoechst Ag, 6230 Frankfurt | Derivate der cis, endo-2-azabicyclo-(3.3.0)-octan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung |
NZ202903A (en) * | 1981-12-29 | 1988-01-08 | Hoechst Ag | 1-- pe pyrrol-2-yl-carboxylic acid derivatives and pharmaceutical compositions |
DE3246503A1 (de) * | 1982-12-16 | 1984-06-20 | Hoechst Ag, 6230 Frankfurt | Derivate der cis, endo-2-azabicyclo-(5.3.0)-decan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung |
DE3303112A1 (de) * | 1983-01-31 | 1984-08-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur racemattrennung optisch aktiver bicyclischer imino-(alpha)-carbonsaeuren |
US5175306A (en) * | 1983-01-31 | 1992-12-29 | Hoechst Aktiengesellschaft | Process for the resolution of racemates of optically active bicyclic imino-α-carboxylic esters |
DE3303344A1 (de) | 1983-02-02 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von n-alkylierten aminosaeuren und deren estern |
DE3324263A1 (de) * | 1983-07-06 | 1985-01-17 | Hoechst Ag, 6230 Frankfurt | Derivate der 2-azabicyclo(3.1.0)hexan-3-carbonsaeure, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung sowie 2-azabicyclo(3.1.0)hexan-derivate als zwischenprodukte und verfahren zu deren herstellung |
DE3333455A1 (de) * | 1983-09-16 | 1985-04-11 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung n-alkylierter dipeptide und deren estern |
DE3333454A1 (de) * | 1983-09-16 | 1985-04-11 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von n-alkylierten dipeptiden und deren estern |
DE3410732A1 (de) * | 1984-03-23 | 1985-09-26 | Hoechst Ag, 6230 Frankfurt | Methode zur behandlung des glaukoms |
DE3413710A1 (de) * | 1984-04-12 | 1985-10-24 | Hoechst Ag, 6230 Frankfurt | Verfahren zur behandlung der herzinsuffizienz |
US5684016A (en) * | 1984-04-12 | 1997-11-04 | Hoechst Aktiengesellschaft | Method of treating cardiac insufficiency |
EP0190224A1 (en) * | 1984-07-30 | 1986-08-13 | Schering Corporation | PROCESS FOR THE PREPARATION OF CIS, ENDOOCTAHYDROCYCLOPENTA [b] PYRROLE-2-CARBOXYLATE |
DE3431541A1 (de) * | 1984-08-28 | 1986-03-06 | Hoechst Ag, 6230 Frankfurt | Cis,endo-2-azabicycloalkan-3-carbonsaeure-derivate, verfahren zu deren herstellung, deren verwendung sowie zwischenprodukte bei deren herstellung |
US4925969A (en) * | 1985-02-04 | 1990-05-15 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Process for preparing ethyl-alpha-amino-gamma-oxo-gamma-phenybutyrate derivatives |
EP0190687B1 (en) * | 1985-02-04 | 1988-10-05 | Kanegafuchi Kagaku Kogyo Kabushiki Kaisha | Process for preparing ethyl-alpha-(1-carboxyethyl)-amino-gamma-oxo-gamma-phenylbutyrate |
US4762821A (en) * | 1985-03-22 | 1988-08-09 | Syntex (U.S.A.) Inc. | N',N"-dialkylguanidino dipeptides |
DE3518514A1 (de) * | 1985-05-23 | 1986-11-27 | Hoechst Ag, 6230 Frankfurt | Neue derivate bicyclischer aminosaeuren, verfahren zu ihrer herstellung, diese enthaltende mittel und deren verwendung |
US5231080A (en) * | 1985-10-15 | 1993-07-27 | Hoechst Aktiengesellschaft | Method for the treatment of atherosclerosis, thrombosis, and peripheral vessel disease |
DE3770301D1 (de) * | 1986-03-27 | 1991-07-04 | Kanegafuchi Chemical Ind | N2-(1-carboxy-3-oxo-3-phenylpropyl)-l-lysinverbindungen und deren abkoemmlinge. |
US5231084A (en) * | 1986-03-27 | 1993-07-27 | Hoechst Aktiengesellschaft | Compounds having a cognition adjuvant action, agents containing them, and the use thereof for the treatment and prophylaxis of cognitive dysfuncitons |
EP0254032A3 (en) | 1986-06-20 | 1990-09-05 | Schering Corporation | Neutral metalloendopeptidase inhibitors in the treatment of hypertension |
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DE3345355A1 (de) * | 1983-12-15 | 1985-06-27 | Hoechst Ag, 6230 Frankfurt | Verfahren zur racematspaltung bicyclischer imino-(alpha)-carbonsaeureester |
EP0190224A1 (en) * | 1984-07-30 | 1986-08-13 | Schering Corporation | PROCESS FOR THE PREPARATION OF CIS, ENDOOCTAHYDROCYCLOPENTA [b] PYRROLE-2-CARBOXYLATE |
JPH074338B2 (ja) * | 1987-02-27 | 1995-01-25 | オリンパス光学工業株式会社 | 内視鏡 |
-
1982
- 1982-07-17 DE DE19823226768 patent/DE3226768A1/de not_active Withdrawn
- 1982-10-03 DZ DZ826703A patent/DZ473A1/fr active
- 1982-11-02 DE DE8484111056T patent/DE3280196D1/de not_active Expired - Lifetime
- 1982-11-02 DE DE8282110070T patent/DE3269875D1/de not_active Expired
- 1982-11-02 EP EP82110070A patent/EP0079022B1/de not_active Expired
- 1982-11-02 EP EP84111056A patent/EP0150263B1/de not_active Expired - Lifetime
- 1982-11-02 LU LU88260C patent/LU88260I2/xx unknown
- 1982-11-03 KR KR8204953A patent/KR890000007B1/ko active
- 1982-11-03 AR AR82291182A patent/AR240675A1/es active
- 1982-11-03 FI FI823757A patent/FI81087C/fi not_active IP Right Cessation
- 1982-11-03 DD DD82244533A patent/DD203047A5/de unknown
- 1982-11-03 DD DD82257322A patent/DD219480A5/de unknown
- 1982-11-03 PT PT75792A patent/PT75792A/pt unknown
- 1982-11-03 GR GR69702A patent/GR77381B/el unknown
- 1982-11-03 IL IL67172A patent/IL67172A/xx not_active IP Right Cessation
- 1982-11-03 ES ES517066A patent/ES517066A0/es active Granted
- 1982-11-03 NZ NZ202378A patent/NZ202378A/en unknown
- 1982-11-04 CS CS827874A patent/CS247159B2/cs unknown
- 1982-11-04 HU HU832908A patent/HU186339B/hu unknown
- 1982-11-04 IE IE2636/82A patent/IE56476B1/en active Protection Beyond IP Right Term
- 1982-11-04 DK DK490482A patent/DK166624C/da not_active IP Right Cessation
- 1982-11-04 AU AU90145/82A patent/AU565200B2/en not_active Expired
- 1982-11-04 HU HU823551A patent/HU186594B/hu unknown
- 1982-11-04 NO NO823674A patent/NO156940C/no not_active IP Right Cessation
- 1982-11-04 CA CA000414858A patent/CA1187087A/en not_active Expired
- 1982-11-05 MA MA19851A patent/MA19639A1/fr unknown
- 1982-11-06 JO JO19821224A patent/JO1224B1/en active
- 1982-12-13 ES ES518132A patent/ES8308541A1/es not_active Expired
- 1982-12-13 ES ES518133A patent/ES8308542A1/es not_active Expired
-
1983
- 1983-04-05 PH PH28735A patent/PH22417A/en unknown
- 1983-12-22 SU SU833679915A patent/SU1277895A3/ru active
-
1984
- 1984-10-09 US US06/658,902 patent/US4727160A/en not_active Expired - Lifetime
- 1984-11-12 PH PH31435A patent/PH21175A/en unknown
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1987
- 1987-02-04 AU AU68509/87A patent/AU586316B2/en not_active Expired
- 1987-02-04 AU AU68510/87A patent/AU585429B2/en not_active Expired
-
1988
- 1988-11-02 US US07/267,753 patent/US4879403A/en not_active Expired - Lifetime
-
1989
- 1989-01-07 SG SG11/89A patent/SG1189G/en unknown
- 1989-01-12 US US07/296,513 patent/US5061722A/en not_active Expired - Lifetime
- 1989-02-28 US US07/318,519 patent/US5053519A/en not_active Expired - Lifetime
- 1989-08-14 JP JP1207997A patent/JPH02104573A/ja active Granted
- 1989-08-14 JP JP1207998A patent/JPH02104526A/ja active Granted
- 1989-09-14 HK HK748/89A patent/HK74889A/xx not_active IP Right Cessation
-
1991
- 1991-03-18 JP JP3077209A patent/JPH0694443B2/ja not_active Expired - Lifetime
- 1991-12-30 CZ CS914162A patent/CZ416291A3/cs unknown
-
1992
- 1992-09-17 DK DK199201144A patent/DK172751B1/da not_active IP Right Cessation
-
1993
- 1993-05-19 NL NL930039C patent/NL930039I2/nl unknown
-
1994
- 1994-02-23 BG BG98537A patent/BG60532B2/bg unknown
-
1995
- 1995-03-03 NO NO1995001C patent/NO1995001I1/no unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11289233B2 (en) | 2016-04-28 | 2022-03-29 | Kepco Nuclear Fuel Co., Ltd. | Method for collecting uranium by treatment process of washing waste liquid generated in uranium hexafluoride cylinder washing process |
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