KR950032116A - 폴리요오드화 화합물, 이의 제조방법과 진단용 조성물 - Google Patents
폴리요오드화 화합물, 이의 제조방법과 진단용 조성물 Download PDFInfo
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- KR950032116A KR950032116A KR1019950006139A KR19950006139A KR950032116A KR 950032116 A KR950032116 A KR 950032116A KR 1019950006139 A KR1019950006139 A KR 1019950006139A KR 19950006139 A KR19950006139 A KR 19950006139A KR 950032116 A KR950032116 A KR 950032116A
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- 150000001875 compounds Chemical class 0.000 title claims 20
- 239000000203 mixture Substances 0.000 title claims 4
- 238000002360 preparation method Methods 0.000 title 1
- 150000001414 amino alcohols Chemical class 0.000 claims abstract 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 9
- 238000000034 method Methods 0.000 claims 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 2
- 230000003213 activating effect Effects 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000026045 iodination Effects 0.000 claims 2
- 238000006192 iodination reaction Methods 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- YFOMJTXVFXURLQ-UHFFFAOYSA-N 1,3-diiodo-2-methyl-5-nitrobenzene Chemical compound CC1=C(I)C=C([N+]([O-])=O)C=C1I YFOMJTXVFXURLQ-UHFFFAOYSA-N 0.000 claims 1
- JNETYVLEGPSOFY-UHFFFAOYSA-N 3-bromopyrrolidine-2,5-dione Chemical compound BrC1CC(=O)NC1=O JNETYVLEGPSOFY-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- GZUXJHMPEANEGY-BJUDXGSMSA-N bromomethane Chemical class Br[11CH3] GZUXJHMPEANEGY-BJUDXGSMSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- -1 carboxylic acid compound Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/12—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to hydrocarbon groups substituted by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/68—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/69—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Saccharide Compounds (AREA)
- Detergent Compositions (AREA)
Abstract
본 발명은 진단용 X-선 건사하는데 조영제로로서 사용될 수 있는 다음 일반식의 화합물에 관한 것이다.
상기식에서 R1, R2, R3, R4, R5, R6는 각각 요오드원자와 다음식의 기에서 선택한다
상기식들에서 A는 아무것도 나타내지 않거나 임의로 히드록실화되는 (C1-C4)알킬렌을 나타내며; R7, R8, R9, R10, R11과 R12는 같거나 다른 것으로 H, 임의로 히드록실화되거나 또는 임의로 히드록실화되는 하나 또는 그 이상의 (C1-C3)알콕시기를 갖거나 또는 이들에 결합되는 질소원자를 갖는 (C1-C10)알킬을 나타내며, R7과 R8, R9과 R10또는 R11과 R12는 임의로 히드록실화되는 5-내지 8-원환 포화헤테로 고리를 독립적으로 형성할 수 있으며, 이때 R1, R2, R3, R4, R5와 R6중에서 최소한 4개의 기는 요오드원자를 나타내고 일반식(I)의 화합물은 1O~24개의 히드록실기를 함유하며 알킬, 알콕시, 알킬렌기는 선형 또는 선형 또는 분자형이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (20)
- 다음 일반식의 화합물상기식에서 R1, R2, R3, R4, R5, R6는 각각 요오드원자와 다음식의 기에서 선택한다상기식들에서 A는 아무것도 나타내지 않거나 임의로 히드록실화되는 (C1-C4)알킬렌을 나타내며; R7, R8, R9, R10, R11과 R12는 같거나 다른 것으로 H, 임의로 히드록실화되거나 또는 임의로 히드록실화되는 하나 또는 그 이상의 (C1-C3)알콕시기를 갖거나 또는 이들에 결합되는 질소원자를 갖는 (C1-C10)알킬을 나타내며, R7, R8, R9과 R10또는 R11과 R12는 임의로 히드록실화되는 5-내지 8-원환 포화헤테로 고리를 독립적으로 형성할 수 있으며, 이때 R1, R2, R3, R4, R5와 R6중에서 최소한 4개의 기는 요오드원자를 나타내고 일반식(I)의 화합물은 10~24개의 히드록실기를 함유하며 알킬, 알콕시, 알킬렌기는 선형 또는 선형 또는 분자형이다.
- 제1항에 있어서, 화합물이 테트라요오드화되고 다른 두개의 치환기가 각각(상기식에서 A는 CH2또는 아무것도 아니고 R7, R8, R9,과 R|10은 제1항에서 정의한 바와 같다)을 나타냄을 특징으로 하는 일반식(I)의 화합물.
- 제1항에 있어서, A는 아무것도 아니고, R2=R3=R5=R6=I이고 R|4는 각각 히드록실화된 CO-NR7R8기 또는 히드록실화된 N(R10)-CO-R9기를 나타내고 화합물이 12~20개의 히드록실기를 나타내는 일반식(I)의 화합물.
- 제1항에 있어서, R2=R3=R5=R6=I; R1=R4는 각각 CO-NR7R8기 또는 N(R10)-CO-R9를 나타내고 여기서, R7, R8, R9와 R10은 서로 독립적으로 -(CH|2)m-(CH0H)n-CH2OH (m=1 또는 2, n=O~4),또는 -C-(CH2OH3)를 나타내고 12~16개의 히드록실기를 함유하는 일반식 (I)의 화합물.
- 5제1항에 있어서, 다음 일반식(Ⅲ)의 화합물:상기식에서 R7, R8, R'7, R'8는 같거나 다른 것으로, 일반식(I)의 R7, R8의 의미를 갖는다.
- 제5항에 있어서, 두개의 아미드기가 다르고 각각 최소한 두개의 히드록실기를 함유하는 일반식(Ⅱ)의 화합물.
- 제5항에 있어서, 두 아미드가 동일한 일반식(Ⅱ)의 화합물.
- 제5항에 있어서, 두 아미드가 동일하고 R7, R8, R′7R′8을 -(CH2)m-(CH0H)n-CH2OH (m=1 또는 2, n=O~4),또는 -C-(CH2OH)3에서 선택하고 12~20개의 히드록실기를 함유하는 일반식 (Ⅱ)의 화합물.
- 제5항에 있어서, NR7R8과 NR′7R′8은 동일하고 R7, R8, R′7R′8을 CH2-(CH0H)n-CH2OH (n=O~4),또는 -C-(CH2OH)3에서 선택하고 12~20개의 히드록실기를 함유하는 일반식 (Ⅱ)의 화합물.
- 제5항에 있어서, NR7R8과 NR′7R′8은 동일하고 R7, R8, R′7R′8을 CH2-(CH0H)n-CH2OH (n=O~3) 선택하고 일반식(Ⅱ)의 화합물이 12~20개의 히드록실기를 함유하는 일반식 (Ⅱ)의 화합물.
- 제5항에 있어서, NR7R8과 NR′R′7R′8이를 나타내는 일반식 (Ⅱ)의 화합물.
- 제5항에 있어서, NR7R8과 NR′R′7R′8이를 나타내는 일반식 (Ⅱ)의 화합물.
- 대응하는 카트복실산 화합물의 활성화 유도제를 적당한 아미노 알코올과 반응시킴을 특징으로 하는 치환기를 요오드원자와 다음기;(상기식에서 R7과 R8은 같거나 다른것으로, 제1항과 동일한 의미를 갖고 A는 제1항에서 정의한 바와 같다)에서 선택되는 일반식(I)의 화합물의 제조방법,
- R2=R3=R5=R6=I;(상기식에서 R7, R8, R9, R10이 같거나 다른것으로, 제1항에서와 동일한 의미를 갖는다)인 일반식(I)의 테트파요오드화 화합물의 제조방법에 있어서, 1/P-니트론톨루엔을 요오드화하여 2,6-디요오드-4-니트로톨루엔을 얻는 단계; 2/N-브론모석신이미드를 반응시켜서 다음식의 화합물을 얻는 단계;3/브톰화 유도체를 산화시켜서 2,6-디요오도-4-니트론벤즈알테히드를 얻은 다음 2,6-디요오도-4-니트론벤조산을 얻은 단계; 4/앞단계에서 얻은 산의 활성화 유도체를 아미노알코을 HNR7R8과 반응시키는 단계; 5/니트론기를 아미노를 촉매 환원시키는 단계; 6/앞 단계에서 얻은 아닐핀을 요오도화하는 단계; 7/산 R9-COOH의 활성화 유도제를 생성된 요오드와 화합물과 반응시키고, 히드록실기를 임의로 보호하는 단계 8/일반식 R10-X″ (여기서 X″는 할로겐, (C1-C4)알킬술폰일 또는 (C6-C10)아릴술폰일기를 나타낸다)의 화합물을 반응시켜서 4차 아민을 얻는 단계; 9/히드록실기를 임의로 탈보호하는 단계로 이루어짐을 특징으로 하는 상기 제조방법.
- 제약학적으로 허용될 수 있는 부형제와 조합되고, 활성제로서 제1항 내지 제12항 중 어느 한 항에 따른 화합물을 함유하는 X선 검사를 위한 진단용 조성물.
- 제l5항에 있어서, 활성성분으로서, 다음식의 화합물;(상기식에서 R7과 R8을 각각와 -CH-(CHOH)9-CH2OH(P=1 또는 3)에서 선택한다)을 함유함을 특징으로 하는 진단용 조성물.
- 제15항에 있어서, 활성성분으로서, 다음 일반식의 화합물;(상기식에서 R7과 R8을 각각 -CH2-(CHOH)NCH2OH(n=0~3)에서 선택하고, 이는 12~16개의 히드록실기를 함유한다.)을 함유함을 특징으로 하는 진단용 조성물.
- 다음식의 아미노 알코올 ;(여기서 n=1~3)
- 다음식의 아미노 알코올 ;(여기서 R=CH2(CHOH)P-CH2OH, P=2,3)
- 다음식의 아미노 알코올 ;(여기에서 R=CH2-(CHOH)P-CH2OH, P=1~3)※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR94.03356 | 1994-03-22 | ||
| FR9403356A FR2717799B1 (fr) | 1994-03-22 | 1994-03-22 | Composés polyiodes : procédé de préparation ; composition de diagnostic. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR950032116A true KR950032116A (ko) | 1995-12-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950006139A KR950032116A (ko) | 1994-03-22 | 1995-03-22 | 폴리요오드화 화합물, 이의 제조방법과 진단용 조성물 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5693311A (ko) |
| EP (1) | EP0675105B1 (ko) |
| JP (1) | JPH07316112A (ko) |
| KR (1) | KR950032116A (ko) |
| CN (1) | CN1112548A (ko) |
| AT (1) | ATE174902T1 (ko) |
| AU (1) | AU694164B2 (ko) |
| BR (1) | BR9501157A (ko) |
| CA (1) | CA2145035A1 (ko) |
| CZ (1) | CZ69595A3 (ko) |
| DE (1) | DE69506760T2 (ko) |
| ES (1) | ES2126224T3 (ko) |
| FI (1) | FI951323A (ko) |
| FR (1) | FR2717799B1 (ko) |
| HU (1) | HUT71893A (ko) |
| IL (1) | IL112985A (ko) |
| NO (1) | NO951072L (ko) |
| NZ (1) | NZ270750A (ko) |
| ZA (1) | ZA952265B (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2780287B3 (fr) * | 1998-06-30 | 2000-09-08 | Guerbet Sa | Derive polyhydroxyle du tetraiodoterephtalamide, son procede de preparation, son utilisation en radiologie et amino alcool intermediaire |
| US20060100127A1 (en) * | 2004-11-11 | 2006-05-11 | Meier Ingrid K | N,N-dialkylpolyhydroxyalkylamines |
| CN101820923A (zh) | 2007-10-12 | 2010-09-01 | 通用电气医疗集团股份有限公司 | 对比剂 |
| DE102007058220A1 (de) | 2007-12-03 | 2009-06-04 | Bayer Schering Pharma Aktiengesellschaft | Dimere macrocyclisch substituierte Benzolderivate |
| CN103086915A (zh) * | 2011-10-31 | 2013-05-08 | 上海海神化学生物科技有限公司 | 制备3,5-二取代-2,4,6-三碘代芳香胺类化合物的碘化方法 |
| WO2017165841A1 (en) | 2016-03-25 | 2017-09-28 | Nanoprobes, Inc. | Iodine-based particles |
| US10342232B1 (en) | 2018-10-24 | 2019-07-09 | The United States Of America As Represented By The Secretary Of The Navy | Iodinated polymers for biological agent defeat |
| CN114262279B (zh) * | 2021-12-30 | 2022-12-16 | 上海汇禾医疗科技有限公司 | 一种x射线可显影分子、栓塞微球及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH385423A (de) * | 1958-12-03 | 1964-12-15 | Chemie Linz Ag | Verwendung polyjodierter Benzoesäureabkömmlinge als Röntgenkontrastmittel |
| DE2909439A1 (de) * | 1979-03-08 | 1980-09-18 | Schering Ag | Neue nichtionische roentgenkontrastmittel |
| IT1245853B (it) * | 1990-11-16 | 1994-10-25 | Bracco Spa | 1,3-bis(3-(mono o poliidrossi)acilamino-5-(mono o poliidrossi-alchil) aminocarbonil-2,4,6-triiodo-benzoil-amino)-idrossi- o idrossi-alchil- propani, loro metodo di preparazione e mezzi di contrasto roentgenografici che li contengono |
| FR2687669B1 (fr) * | 1992-02-24 | 1997-12-19 | Guerbet Sa | Composes utilisables dans des produits de contraste pour la radiographie. |
-
1994
- 1994-03-22 FR FR9403356A patent/FR2717799B1/fr not_active Expired - Fee Related
-
1995
- 1995-03-14 IL IL11298595A patent/IL112985A/xx not_active IP Right Cessation
- 1995-03-17 US US08/406,304 patent/US5693311A/en not_active Expired - Lifetime
- 1995-03-17 CZ CZ95695A patent/CZ69595A3/cs unknown
- 1995-03-17 JP JP7058753A patent/JPH07316112A/ja active Pending
- 1995-03-20 ES ES95400611T patent/ES2126224T3/es not_active Expired - Lifetime
- 1995-03-20 ZA ZA952265A patent/ZA952265B/xx unknown
- 1995-03-20 DE DE69506760T patent/DE69506760T2/de not_active Expired - Fee Related
- 1995-03-20 EP EP95400611A patent/EP0675105B1/fr not_active Expired - Lifetime
- 1995-03-20 CA CA002145035A patent/CA2145035A1/en not_active Abandoned
- 1995-03-20 AT AT95400611T patent/ATE174902T1/de not_active IP Right Cessation
- 1995-03-20 NZ NZ270750A patent/NZ270750A/en unknown
- 1995-03-21 FI FI951323A patent/FI951323A/fi unknown
- 1995-03-21 CN CN95102715A patent/CN1112548A/zh active Pending
- 1995-03-21 HU HU9500823A patent/HUT71893A/hu unknown
- 1995-03-21 AU AU14990/95A patent/AU694164B2/en not_active Ceased
- 1995-03-21 NO NO951072A patent/NO951072L/no not_active Application Discontinuation
- 1995-03-22 KR KR1019950006139A patent/KR950032116A/ko not_active Application Discontinuation
- 1995-03-22 BR BR9501157A patent/BR9501157A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FI951323A (fi) | 1995-09-23 |
| FI951323A0 (fi) | 1995-03-21 |
| AU694164B2 (en) | 1998-07-16 |
| NZ270750A (en) | 1996-05-28 |
| NO951072D0 (no) | 1995-03-21 |
| JPH07316112A (ja) | 1995-12-05 |
| NO951072L (no) | 1995-09-25 |
| DE69506760T2 (de) | 1999-09-02 |
| AU1499095A (en) | 1995-09-28 |
| ATE174902T1 (de) | 1999-01-15 |
| EP0675105A1 (fr) | 1995-10-04 |
| FR2717799A1 (fr) | 1995-09-29 |
| US5693311A (en) | 1997-12-02 |
| HUT71893A (en) | 1996-02-28 |
| ZA952265B (en) | 1996-09-20 |
| CN1112548A (zh) | 1995-11-29 |
| BR9501157A (pt) | 1996-06-04 |
| IL112985A (en) | 1999-10-28 |
| EP0675105B1 (fr) | 1998-12-23 |
| ES2126224T3 (es) | 1999-03-16 |
| CA2145035A1 (en) | 1995-09-23 |
| HU9500823D0 (en) | 1995-05-29 |
| DE69506760D1 (de) | 1999-02-04 |
| IL112985A0 (en) | 1995-06-29 |
| FR2717799B1 (fr) | 1996-07-19 |
| CZ69595A3 (en) | 1995-11-15 |
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