KR900016097A - 치료활성도를 가지는 시클로메틸렌-1,2-비카르복시산의 아미드, 이의 제조방법 및 이를 포함하는 제약학적 조성물 - Google Patents
치료활성도를 가지는 시클로메틸렌-1,2-비카르복시산의 아미드, 이의 제조방법 및 이를 포함하는 제약학적 조성물 Download PDFInfo
- Publication number
- KR900016097A KR900016097A KR1019890004818A KR890004818A KR900016097A KR 900016097 A KR900016097 A KR 900016097A KR 1019890004818 A KR1019890004818 A KR 1019890004818A KR 890004818 A KR890004818 A KR 890004818A KR 900016097 A KR900016097 A KR 900016097A
- Authority
- KR
- South Korea
- Prior art keywords
- carbonyl
- oxoethyl
- hydroxyamino
- acid
- cis
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims 11
- 150000001408 amides Chemical class 0.000 title claims 3
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 22
- 238000000034 method Methods 0.000 claims 19
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 13
- -1 hydroxy Hydroxyamino Chemical group 0.000 claims 13
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 claims 11
- 230000005494 condensation Effects 0.000 claims 11
- 238000009833 condensation Methods 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 5
- 238000002054 transplantation Methods 0.000 claims 5
- ODPRAEVXIDWHGI-UHFFFAOYSA-N 2-(oxomethylidene)cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCCCC1=C=O ODPRAEVXIDWHGI-UHFFFAOYSA-N 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 150000008064 anhydrides Chemical class 0.000 claims 3
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 125000003368 amide group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- UTTOWNNYNRJPBF-YGFGXBMJSA-N (1r,2r)-2-[[1-(hydroxyamino)-1-oxo-4-phenylbutan-2-yl]-methylcarbamoyl]cyclohexane-1-carboxylic acid Chemical compound O=C([C@H]1[C@@H](CCCC1)C(O)=O)N(C)C(C(=O)NO)CCC1=CC=CC=C1 UTTOWNNYNRJPBF-YGFGXBMJSA-N 0.000 claims 1
- GQRQILVWCFCYCH-CFCGPWAMSA-N (1r,2r)-2-[[1-(hydroxyamino)-1-oxopropan-2-yl]-methylcarbamoyl]cyclohexane-1-carboxylic acid Chemical compound ONC(=O)C(C)N(C)C(=O)[C@@H]1CCCC[C@H]1C(O)=O GQRQILVWCFCYCH-CFCGPWAMSA-N 0.000 claims 1
- QKIVRALZQSUWHH-HTQZYQBOSA-N (1r,2r)-2-[[2-(hydroxyamino)-2-oxoethyl]-methylcarbamoyl]cyclohexane-1-carboxylic acid Chemical compound ONC(=O)CN(C)C(=O)[C@@H]1CCCC[C@H]1C(O)=O QKIVRALZQSUWHH-HTQZYQBOSA-N 0.000 claims 1
- PJHAKRAYWRQDBE-NXEZZACHSA-N (1r,2r)-2-[[2-(hydroxyamino)-2-oxoethyl]-propan-2-ylcarbamoyl]cyclohexane-1-carboxylic acid Chemical compound ONC(=O)CN(C(C)C)C(=O)[C@@H]1CCCC[C@H]1C(O)=O PJHAKRAYWRQDBE-NXEZZACHSA-N 0.000 claims 1
- AHDXOBSQZGFFDM-NXEZZACHSA-N (1r,2r)-2-[[2-(hydroxyamino)-2-oxoethyl]-propylcarbamoyl]cyclohexane-1-carboxylic acid Chemical compound ONC(=O)CN(CCC)C(=O)[C@@H]1CCCC[C@H]1C(O)=O AHDXOBSQZGFFDM-NXEZZACHSA-N 0.000 claims 1
- BMSGFEVGHRIDSM-YGFGXBMJSA-N (1r,2r)-2-[ethyl-[1-(hydroxyamino)-1-oxo-3-phenylpropan-2-yl]carbamoyl]cyclohexane-1-carboxylic acid Chemical compound O=C([C@H]1[C@@H](CCCC1)C(O)=O)N(CC)C(C(=O)NO)CC1=CC=CC=C1 BMSGFEVGHRIDSM-YGFGXBMJSA-N 0.000 claims 1
- ZPMKITFPNZSTHS-NXEZZACHSA-N (1r,2r)-2-[ethyl-[3-(hydroxyamino)-3-oxopropyl]carbamoyl]cyclohexane-1-carboxylic acid Chemical compound ONC(=O)CCN(CC)C(=O)[C@@H]1CCCC[C@H]1C(O)=O ZPMKITFPNZSTHS-NXEZZACHSA-N 0.000 claims 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical group CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
- CXNFOKYCSXHBFJ-UHFFFAOYSA-N 2-(oxomethylidene)cyclopentane-1-carboxylic acid Chemical compound OC(=O)C1CCCC1=C=O CXNFOKYCSXHBFJ-UHFFFAOYSA-N 0.000 claims 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical group C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- QCGAWMMKNHWYKB-UHFFFAOYSA-N C1(=CC=CC=C1)CCC(C(=O)NO)NC(=O)C1(CCCC1)C(=O)O Chemical compound C1(=CC=CC=C1)CCC(C(=O)NO)NC(=O)C1(CCCC1)C(=O)O QCGAWMMKNHWYKB-UHFFFAOYSA-N 0.000 claims 1
- USGWCYUCOKWQKM-UHFFFAOYSA-N C1CCC(CC1)(C(=O)NC(CCC2=CC=CC=C2)C(=O)NO)C(=O)O Chemical compound C1CCC(CC1)(C(=O)NC(CCC2=CC=CC=C2)C(=O)NO)C(=O)O USGWCYUCOKWQKM-UHFFFAOYSA-N 0.000 claims 1
- BYTQGBGCDLEORU-UHFFFAOYSA-N C1CCC(CC1)(C(=O)NC(CCCC2=CC=CC=C2)C(=O)NO)C(=O)O Chemical compound C1CCC(CC1)(C(=O)NC(CCCC2=CC=CC=C2)C(=O)NO)C(=O)O BYTQGBGCDLEORU-UHFFFAOYSA-N 0.000 claims 1
- QYTJQINCMPFKNO-UHFFFAOYSA-N CC(C(=O)NO)N(C)C(=O)C1(CCCCC1)C(=O)O Chemical compound CC(C(=O)NO)N(C)C(=O)C1(CCCCC1)C(=O)O QYTJQINCMPFKNO-UHFFFAOYSA-N 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- TUUCRHWZNKHNSZ-DTWKUNHWSA-N methyl (1r,2s)-2-[[2-(hydroxyamino)-2-oxoethyl]-methylcarbamoyl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1CCCC[C@@H]1C(=O)N(C)CC(=O)NO TUUCRHWZNKHNSZ-DTWKUNHWSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/61—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than 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 doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
- Eyeglasses (AREA)
- Polyamides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20172A/88 | 1988-04-02 | ||
| IT8820172A IT1224627B (it) | 1988-04-12 | 1988-04-12 | Ammidi di acidi ciclometilen_1,2_dicarbossilici adattivita' terapeutica, procedimenti per la loro preparazione e composizioni farmaceutiche che le contengono. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR900016097A true KR900016097A (ko) | 1990-11-12 |
Family
ID=11164400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890004818A KR900016097A (ko) | 1988-04-12 | 1989-04-12 | 치료활성도를 가지는 시클로메틸렌-1,2-비카르복시산의 아미드, 이의 제조방법 및 이를 포함하는 제약학적 조성물 |
Country Status (28)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1252708B (it) * | 1991-12-23 | 1995-06-26 | Guidotti & C Spa Labor | Sali stabili dell'acido (+)-(1r,2s)-2((n-(2-idrossilammino-2-ossoetil)-n-metilammino)carbonil)cicloesan-1-carbossilico,ad attivita' ace inibitrice, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono. |
| US5977160A (en) * | 1992-04-10 | 1999-11-02 | Brigham And Women's Hospital, Inc. | Methods for reducing risk of repeat myocardial infarction and increasing survival in heart attack victims |
| IT1264860B1 (it) * | 1993-06-21 | 1996-10-17 | Guidotti & C Spa Labor | Derivati di acidi cis- e trans-2(((2-(isdrossiammino)-2-ossoetil)- alchilammino)carbonil)cicloesancarbossilici |
| US5639746A (en) * | 1994-12-29 | 1997-06-17 | The Procter & Gamble Company | Hydroxamic acid-containing inhibitors of matrix metalloproteases |
| US6028213A (en) * | 1998-04-16 | 2000-02-22 | Eastman Chemical Company | Optically active cis-1,3-cyclohexanedicarboxylic acid monoesters with high enantiomeric purity and process for their preparation |
| CA2658913C (en) * | 2006-07-24 | 2015-07-21 | Ucb Pharma S.A. | Substituted aniline derivatives |
| US8106221B2 (en) | 2007-06-20 | 2012-01-31 | Vitae Pharmaceuticals, Inc. | Renin inhibitors |
| WO2008156831A2 (en) * | 2007-06-20 | 2008-12-24 | Vitae Pharmaceuticals, Inc. | Renin inhibitors |
| US8361438B2 (en) | 2008-01-08 | 2013-01-29 | Lantheus Medical Imaging, Inc. | N-alkoxyamide conjugates as imaging agents |
| JP5676600B2 (ja) | 2009-07-08 | 2015-02-25 | ランセウス メディカル イメージング， インコーポレイテッド | 造影剤としてのｎ−アルコキシアミド抱合体 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4077998A (en) * | 1975-10-28 | 1978-03-07 | Morton-Norwich Products, Inc. | Phthaloyl amino acid hydroxamic acids |
| US4687841A (en) * | 1985-10-18 | 1987-08-18 | Monsanto Company | Peptide hydroxamic acid derivatives |
-
1988
- 1988-04-12 IT IT8820172A patent/IT1224627B/it active
-
1989
- 1989-04-10 AT AT89106304T patent/ATE101126T1/de not_active IP Right Cessation
- 1989-04-10 DE DE68912811T patent/DE68912811T2/de not_active Expired - Fee Related
- 1989-04-10 IL IL89895A patent/IL89895A0/xx not_active IP Right Cessation
- 1989-04-10 ES ES89106304T patent/ES2061759T3/es not_active Expired - Lifetime
- 1989-04-10 EP EP89106304A patent/EP0337348B1/en not_active Expired - Lifetime
- 1989-04-11 UA UA4614855A patent/UA15920A/uk unknown
- 1989-04-11 HU HU891735A patent/HU206194B/hu not_active IP Right Cessation
- 1989-04-11 FI FI891712A patent/FI891712A/fi not_active Application Discontinuation
- 1989-04-11 RU SU894613962A patent/RU2004538C1/ru active
- 1989-04-11 NZ NZ228688A patent/NZ228688A/en unknown
- 1989-04-11 CA CA000596331A patent/CA1314903C/en not_active Expired - Fee Related
- 1989-04-11 NO NO891484A patent/NO177851C/no unknown
- 1989-04-11 PT PT90254A patent/PT90254B/pt not_active IP Right Cessation
- 1989-04-11 DK DK173689A patent/DK173689A/da not_active IP Right Cessation
- 1989-04-12 BG BG88028A patent/BG60556B1/bg unknown
- 1989-04-12 DD DD89327552A patent/DD294014A5/de not_active IP Right Cessation
- 1989-04-12 ZA ZA892674A patent/ZA892674B/xx unknown
- 1989-04-12 IN IN283/CAL/89A patent/IN169836B/en unknown
- 1989-04-12 CN CN89102213A patent/CN1037344A/zh active Pending
- 1989-04-12 YU YU00738/89A patent/YU73889A/xx unknown
- 1989-04-12 PL PL1989278804A patent/PL159413B1/pl unknown
- 1989-04-12 AU AU32655/89A patent/AU611796B2/en not_active Ceased
- 1989-04-12 JP JP1092774A patent/JPH026452A/ja active Pending
- 1989-04-12 MX MX1563589A patent/MX15635A/es unknown
- 1989-04-12 KR KR1019890004818A patent/KR900016097A/ko not_active Application Discontinuation
- 1989-04-12 RO RO139231A patent/RO104347B1/ro unknown
- 1989-08-28 RU SU894614855A patent/RU1838294C/ru active
-
1990
- 1990-10-09 US US07/595,639 patent/US5095137A/en not_active Expired - Fee Related
- 1990-11-29 IN IN1000/CAL/90A patent/IN172059B/en unknown
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