FI91150B - Förfarande för framställning av nya terapeutiskt användbara 4,5,6-substituerade N-(substituerad-fenyl)-2-pyrimidinaminer - Google Patents
Förfarande för framställning av nya terapeutiskt användbara 4,5,6-substituerade N-(substituerad-fenyl)-2-pyrimidinaminer Download PDFInfo
- Publication number
- FI91150B FI91150B FI870113A FI870113A FI91150B FI 91150 B FI91150 B FI 91150B FI 870113 A FI870113 A FI 870113A FI 870113 A FI870113 A FI 870113A FI 91150 B FI91150 B FI 91150B
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- Finland
- Prior art keywords
- pyridinyl
- phenyl
- methyl
- pyrimidinamine
- alkyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
- A61P11/14—Antitussive agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- 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
-
- 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
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Dental Preparations (AREA)
Claims (9)
1. Förfarande för framställning av nya terapeu-tiskt användbara 4,5,6-substituerade N-(substituerad-fe-5 nyl)-2-pyrimidinaminer med formeln I och deras farmakolo-giskt godtagbara syraadditionssalter f1 /K ^ 1 -R2
10 R4“^4/3N (I) R3 i vilken formel R3 är väte, alkyl(Cj-C3) eller N,N-dime-15 tylaminoetyl; R2 är mono- eller polysubstituerad fenyl, väri substituenterna är alkyl (Ci-Cs), alkoxi(C3-C3), klor, brom, jodi, trifluonnetyl, hydroxi, fenyl, amino, monoalkyl(C1-C3)amino, dialkyl(C1-C3)amino, alkyl(Cj-Cj)keto, propenyloxi, karboxyl, oxiättiksyra, oxiättiksyra-20 etylester, sulfonamido, NjN-dialkylCC^-CaJsulfonamido, N- metylpiperazinyl, piperidinyl, lH-imidazol-l-yl, eller g-rupper, vars formler är O 0 R
25 -CO-R, -NH-C-R, -NR-C-R, -0-(CH_) -NC^_ 1. n A R NHCHO N-OH N-OCH-, n / I II H 3 -C-NH-(CH2)n-N , -CH-CHj, -C-CH3, -C-CH3 30 Γ2 ° /-\ -CH-CH-, -NHCH--C-N <. , -N N ~V 3 2 \_/ R6 -(CH_)m-R.,, -X-(CH„)m-R, ja S / \ 27 1 ' -X-CH--C-N' N-Rp 35 2 \_/ 8 II 91150 111 väri R är alkyl(C1-C3), X är syre (-0-) eller svavel (-S-), m är 1 - 3, n är 2 eller 3, R6 är väte, alkyl-(Ci-Cj), alkoxiiCj-Ca), klor, brom, jodi eller trifluor-metyl, R7 är lH-iraidazol-l-yl eller morfolino ja R8 är 5 alkyl(Ci-Ca), fenyl eller monosubstituerad fenyl, vari substituenterna är alkyl(C^Ca), halogen eller trifluor-metyl; R3 är 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-metyl-3-pyridinyl, 6-metyl-3-pyridinyl, 2-furanyl, 5-me-tyl-2-furanyl, 2,5-dimetyl-3-furanyl, 2-tienyl, 3-tienyl, 10 5-metyl-2-tienyl, 2-fenotiazinyl, 2-pyrazinyl, 2-bensofu-ranyl, 2-(pyridin-N-oxid), 3-(pyridin-N-oxid), 4-(pyridi-n-N-oxid), lH-indol-2-yl, lH-indol-3-yl, 1-metyl-lH-pyr-rol-2-yl, 4-kinolyl, 4-pyridinyl-metyljodidi; R4 är väte eller alkyl(C^-Ca); och R5 är väte eller alkyl-15 (Ci-Ca), kännetecknat därav, att ett alka-noylheteroarylderivat med formeln 0 « R3-C-CH2-R4 20 vari R3 och R4 är definierade ovan, kondenseras med N,N-di(lägrealkyl)formamid eller acetamid(lägrealky1)acetal vid 50 - 150 °C:ssa under 2-24 timmar, varvid 3-di(lägrealkyl )aminoakrylf enon erhälles, vars formel är 25 ? ** Ψ R3-C-CÄ c-N(lägrealkyl)2 som sedan cykliseras med en substituerad fenylguanidin 30 med formeln HN ^R. / V h2n ^r2 35 112 R: och R2 är definierade ovan, i ett neutralt organiskt lösningsmedel vid koktemperatur under 6-48 timmar.
2. Förfarande enligt patentkrav 1, känne-t e c k n a t därav, att man framställer 5 N-[3-(ΙΗ-imidazol-l-yl)fenyl]-4-(4-pyridinyl)-2-pyrimi- dinamin, N-[3-(1H-imidazol-1-y1)fenyl]-4-(2-pyridinyl)-2-pyrimi-dinamin, N,N-dimetyl-N'-[4-metyl-6-(4-pyridinyl)-2-pyrimidinyl]-10 1,4-bensendiamin, Ν' -[4-(2-furanyl)-5-metyl-2-pyrimidinyl]-N,N-dimetyl-l, 4-bensendiamin, N-[4-(dimetylamino)fenyl]-4-(4-pyridinyl)-2-pyrimidin-amin, 15 4-(2-furanyl)-N-(3-metylfenyl)-2-pyrimidinamin, N-[4-[2-(dietylamino)etoxi]fenyl]-4-(4-pyridinyl)-2-pyri-midinamin, N-(4-etylfenyl)-4-(4-pyridinyl)-2-pyrimidinamin, N,N-dimetyl-N'-[4-(3-pyridinyl)-2-pyrimidinyl]-1,4-ben-20 sendiamin, trihydrokloridi, N-[4-( lH-imidazol-l-yl)fenyl]-4-(3-pyridinyl)-2-pyrimidinamin, N-[4-(4-metyl-l-piperazinyl)fenyl]-4-(3-pyridinyl)-2-pyrimidinamin,
25 N-(3-metylfenyl)-4-(4-pyridinyl)-2-pyrimidinamin, N-(4-etylfenyl)-4-(6-metyl-3-pyridinyl)-2-pyrimidinamin, N-(4-etylfenyl)-6-metyl-4-(6-metyl-3-pyridinyl)-2-pyrimidinamin, N-(4-etylfenyl)-4-(2-pyrazinyl)-2-pyrimidinamin,
30 N-( 3-metylfenyl)-4-(2-pyrazinyl)-3-pyrimidinamin, N,N-dimetyl-N'-[4-(3-metyl-2-tienyl)-2-pyrimidinyl]-1,4-bensendiamin eller N-(3-metoxifenyl)-4-(3-metyl-2-tienyl)-2-pyrimidinamin. I!
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US81795186A | 1986-01-13 | 1986-01-13 | |
US81795186 | 1986-01-13 |
Publications (4)
Publication Number | Publication Date |
---|---|
FI870113A0 FI870113A0 (sv) | 1987-01-13 |
FI870113A FI870113A (sv) | 1987-07-14 |
FI91150B true FI91150B (sv) | 1994-02-15 |
FI91150C FI91150C (sv) | 1994-05-25 |
Family
ID=25224278
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI870113A FI91150C (sv) | 1986-01-13 | 1987-01-13 | Förfarande för framställning av nya terapeutiskt användbara 4,5,6-substituerade N-(substituerad-fenyl)-2-pyrimidinaminer |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0233461B2 (sv) |
JP (1) | JPH0780857B2 (sv) |
KR (1) | KR900004693B1 (sv) |
AT (1) | ATE135699T1 (sv) |
AU (2) | AU591223B2 (sv) |
BR (1) | BR1100989A (sv) |
CA (1) | CA1320201C (sv) |
DE (1) | DE3751742T3 (sv) |
DK (1) | DK171251B1 (sv) |
ES (1) | ES2087056T3 (sv) |
FI (1) | FI91150C (sv) |
GR (1) | GR3019455T3 (sv) |
HU (1) | HU198708B (sv) |
IE (1) | IE74202B1 (sv) |
NZ (1) | NZ218924A (sv) |
PH (1) | PH25056A (sv) |
SG (1) | SG47583A1 (sv) |
ZA (1) | ZA87219B (sv) |
Families Citing this family (78)
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BRPI0906799A2 (pt) | 2008-01-11 | 2015-07-14 | Hoffmann La Roche | Moduladores para amiloide beta |
CA2713716A1 (en) * | 2008-02-22 | 2009-08-27 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
WO2010040661A1 (en) | 2008-10-09 | 2010-04-15 | F. Hoffmann-La Roche Ag | Modulators for amyloid beta |
EP2355817A1 (en) | 2008-11-10 | 2011-08-17 | F. Hoffmann-La Roche AG | Heterocyclic gamma secretase modulators |
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US8486967B2 (en) | 2010-02-17 | 2013-07-16 | Hoffmann-La Roche Inc. | Heteroaryl substituted piperidines |
US8334292B1 (en) | 2010-06-14 | 2012-12-18 | Cystic Fibrosis Foundation Therapeutics, Inc. | Pyrimidine compounds and methods of making and using same |
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RU2486180C1 (ru) * | 2011-11-02 | 2013-06-27 | Общество с ограниченной ответственностью "ТехноХим" (ООО "ТехноХим") | Способ получения 2-ариламино-4-гетарилпиримидинов |
WO2014055972A2 (en) * | 2012-10-05 | 2014-04-10 | The Regents Of The University Of California | A new chemical entity useful for treating various diseases |
CN114181199B (zh) * | 2020-09-15 | 2023-09-26 | 成都赜灵生物医药科技有限公司 | 2,4-二取代嘧啶衍生物及其制备方法和用途 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB735702A (en) * | 1952-03-18 | 1955-08-24 | Wellcome Found | Improvements in and relating to 2,4-diaminopyrimidines and methods of making the same |
US4512993A (en) * | 1983-07-25 | 1985-04-23 | Sterling Drug Inc. | 4(Or 5)-(pyridinyl)-2-pyrimidinamines and cardiotonic use thereof |
US4504482A (en) * | 1983-07-28 | 1985-03-12 | Sterling Drug Inc. | [5(or 4)-(Pyridinyl)-2-pyrimidinyl]ureas and cardiotonic use thereof |
GB8412184D0 (en) * | 1984-05-12 | 1984-06-20 | Fisons Plc | Biologically active nitrogen heterocycles |
EP0164204A1 (en) † | 1984-05-12 | 1985-12-11 | FISONS plc | Novel pharmaceutically useful pyrimidines |
US4725600A (en) † | 1984-07-13 | 1988-02-16 | Fujisawa Pharmaceutical Co., Ltd. | Pyrimidine compounds having activity as a cardiotonic anti-hypertensive cerebrovascular vasodilator and anti-platelet aggregation agent |
JPS62501632A (ja) * | 1985-02-05 | 1987-07-02 | ジ・アップジョン・カンパニ− | 4−置換−6−アリ−ルピリミジン化合物 |
US4711888A (en) * | 1985-07-24 | 1987-12-08 | Pfizer Inc. | Hydroxy and alkoxy pyrimidines |
-
1987
- 1987-01-12 ES ES87100277T patent/ES2087056T3/es not_active Expired - Lifetime
- 1987-01-12 SG SG1996002948A patent/SG47583A1/en unknown
- 1987-01-12 AT AT87100277T patent/ATE135699T1/de not_active IP Right Cessation
- 1987-01-12 EP EP87100277A patent/EP0233461B2/en not_active Expired - Lifetime
- 1987-01-12 DE DE3751742T patent/DE3751742T3/de not_active Expired - Fee Related
- 1987-01-13 FI FI870113A patent/FI91150C/sv not_active IP Right Cessation
- 1987-01-13 ZA ZA87219A patent/ZA87219B/xx unknown
- 1987-01-13 JP JP62005867A patent/JPH0780857B2/ja not_active Expired - Lifetime
- 1987-01-13 IE IE7487A patent/IE74202B1/en not_active IP Right Cessation
- 1987-01-13 DK DK015187A patent/DK171251B1/da not_active IP Right Cessation
- 1987-01-13 NZ NZ218924A patent/NZ218924A/en unknown
- 1987-01-13 AU AU67518/87A patent/AU591223B2/en not_active Ceased
- 1987-01-13 HU HU87100A patent/HU198708B/hu not_active IP Right Cessation
- 1987-01-13 CA CA000527173A patent/CA1320201C/en not_active Expired - Fee Related
- 1987-01-13 PH PH34715A patent/PH25056A/en unknown
- 1987-01-15 KR KR1019870000280A patent/KR900004693B1/ko not_active IP Right Cessation
-
1990
- 1990-02-28 AU AU50578/90A patent/AU621461B2/en not_active Ceased
-
1996
- 1996-03-29 GR GR950402384T patent/GR3019455T3/el unknown
-
1997
- 1997-05-14 BR BR1100989-6A patent/BR1100989A/pt active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
IE870074L (en) | 1987-07-13 |
DK15187A (da) | 1987-07-14 |
GR3019455T3 (en) | 1996-06-30 |
PH25056A (en) | 1991-01-28 |
AU6751887A (en) | 1987-07-16 |
ZA87219B (en) | 1987-08-26 |
JPH0780857B2 (ja) | 1995-08-30 |
KR900004693B1 (ko) | 1990-07-02 |
AU5057890A (en) | 1990-07-26 |
IE74202B1 (en) | 1997-07-16 |
FI870113A (sv) | 1987-07-14 |
DE3751742T3 (de) | 2002-11-21 |
CA1320201C (en) | 1993-07-13 |
EP0233461B2 (en) | 2002-05-29 |
DE3751742T2 (de) | 1996-11-21 |
EP0233461B1 (en) | 1996-03-20 |
ATE135699T1 (de) | 1996-04-15 |
JPS62223177A (ja) | 1987-10-01 |
FI91150C (sv) | 1994-05-25 |
DK15187D0 (da) | 1987-01-13 |
DK171251B1 (da) | 1996-08-12 |
AU621461B2 (en) | 1992-03-12 |
ES2087056T3 (es) | 1996-07-16 |
NZ218924A (en) | 1990-04-26 |
FI870113A0 (sv) | 1987-01-13 |
EP0233461A3 (en) | 1988-05-25 |
EP0233461A2 (en) | 1987-08-26 |
HU198708B (en) | 1989-11-28 |
AU591223B2 (en) | 1989-11-30 |
KR870007154A (ko) | 1987-08-17 |
BR1100989A (pt) | 1999-11-09 |
SG47583A1 (en) | 1998-04-17 |
HUT43582A (en) | 1987-11-30 |
DE3751742D1 (de) | 1996-04-25 |
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Legal Events
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BB | Publication of examined application | ||
MM | Patent lapsed |
Owner name: AMERICAN CYANAMID COMPANY |