FI91871B - Förfarande för framställning av som läkemedel användbara derivat av 1H-imidazo/1,2-b/pyrazol - Google Patents
Förfarande för framställning av som läkemedel användbara derivat av 1H-imidazo/1,2-b/pyrazol Download PDFInfo
- Publication number
- FI91871B FI91871B FI893570A FI893570A FI91871B FI 91871 B FI91871 B FI 91871B FI 893570 A FI893570 A FI 893570A FI 893570 A FI893570 A FI 893570A FI 91871 B FI91871 B FI 91871B
- Authority
- FI
- Finland
- Prior art keywords
- group
- pyrazole
- imidazo
- hydrogen
- thienyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- 238000002360 preparation method Methods 0.000 title claims description 17
- 239000003814 drug Substances 0.000 title claims description 10
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title description 6
- 229940079593 drug Drugs 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 109
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 239000003153 chemical reaction reagent Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- -1 phenylsulfonyloxy Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004036 acetal group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- HIGHWDMFFSTQBW-UHFFFAOYSA-N C1=CSC(C2=C3NC=CN3N=C2)=C1 Chemical compound C1=CSC(C2=C3NC=CN3N=C2)=C1 HIGHWDMFFSTQBW-UHFFFAOYSA-N 0.000 claims description 3
- SPMVOOSTCPEXEO-UHFFFAOYSA-N N1C=CN2N=CC=C21 Chemical class N1C=CN2N=CC=C21 SPMVOOSTCPEXEO-UHFFFAOYSA-N 0.000 claims description 3
- SNQIGJUEHBRFIM-UHFFFAOYSA-N C1=CSC(C2=NN3C=CNC3=C2)=C1 Chemical compound C1=CSC(C2=NN3C=CNC3=C2)=C1 SNQIGJUEHBRFIM-UHFFFAOYSA-N 0.000 claims description 2
- CWQDRNQWENBACC-UHFFFAOYSA-N CC1=NN2C=CNC2=C1C1=CC=C(Cl)C=C1 Chemical compound CC1=NN2C=CNC2=C1C1=CC=C(Cl)C=C1 CWQDRNQWENBACC-UHFFFAOYSA-N 0.000 claims description 2
- ORHPRTYFFSOUAR-UHFFFAOYSA-N CC1=NN2C=CNC2=C1C1=CC=CC=C1 Chemical compound CC1=NN2C=CNC2=C1C1=CC=CC=C1 ORHPRTYFFSOUAR-UHFFFAOYSA-N 0.000 claims description 2
- GWNORQZNWYHWKO-UHFFFAOYSA-N CC1=NN2C=CNC2=C1C1=CC=CS1 Chemical compound CC1=NN2C=CNC2=C1C1=CC=CS1 GWNORQZNWYHWKO-UHFFFAOYSA-N 0.000 claims description 2
- XUJNKUAHVXCESR-UHFFFAOYSA-N N=1N2C=CNC2=C(C)C=1C1=CC=CS1 Chemical compound N=1N2C=CNC2=C(C)C=1C1=CC=CS1 XUJNKUAHVXCESR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 abstract description 5
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- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 2
- 125000005018 aryl alkenyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
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- 229910052736 halogen Inorganic materials 0.000 abstract 1
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- 239000000203 mixture Substances 0.000 description 64
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
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- NLYRPESMFJTOLW-UHFFFAOYSA-N 6-phenyl-5h-imidazo[1,2-b]pyrazole Chemical compound C=1C2=NC=CN2NC=1C1=CC=CC=C1 NLYRPESMFJTOLW-UHFFFAOYSA-N 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B17/00—Connecting constructional elements or machine parts by a part of or on one member entering a hole in the other and involving plastic deformation
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Mechanical Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (14)
1. Förfarande för framställning av som läkemedel användbara derivat av 1H-imidazo[1,2-b]pyrazol med formeln (I): 5 R1 R3 R2 C N R*
10. C NC (I) Il I II N N C V där: 15 R1 är en väteatom; en (^-Cg alkylgrupp; en trifluoretylgrupp; en C2-CA alkenylgrupp; en fenylgrupp; en fenylgrupp substituerad med ätminstone en substituent som väljes fran en grupp som bestar av halogenatomer, C1-C2 alkylgrupper, (^-C2 alkoxigrupper, trifluoremetylgrupper och ami-20 nogrupper; en benzylgrupp, en tienylgrupp eller en naftylgrupp; R2 är en väteatom; en C1-CA alkylgrupp; en fenylgrupp; en fenylgrupp substituerad med ätminstone en substituent som väljes frän en grupp som bestar av halogenatomer, C1-C2 alkoxigrupper, trifluormetylgrupper, : 25 hydroxigrupper och benzyloxigrupper; en benzylgrupp, en tienylgrupp, en furylgrupp eller en pyridylgrupp; R3 avser en väteatom; en (^-03 alkylgrupp; en etoxikarbonyl- eller cyano-C1-C3 alkylgrupp; eller en benzylgrupp; 30 R4 är en väteatom eller en etoxikarbonyl-C1-C2-alkylgrupp; och R5 är en väteatom eller en fenylgrupp;
35 MED DEN FÖRUTSÄTTNINGEN ATT: 40 91871 (i) R1 inte avser en väteatom eller en icke-substituerad alkylgrupp da R1 avser en väteatom, en icke-substituerad alkylgrupp eller en fenylgrupp; 5 eller farmaceutiskt acceptabla syraadditionssalter av dessa, k ä n -netecknat därav, att (i) en förening med formeln (II) cykliseras i närvaro av en syra:
10 R1 , I R1 C NH, \ / \ / C NC Y (II) II I II , N_N C-R2 \ / C
15. R5 (där R1, R1, R2 och R5 är definierade som ovan, och gruppen som rep-20 resenteras av >C=Y är en karbonylgrupp eller en acetalgrupp) och sedan, om sa krävs, later man produkten reagera med en förening med formeln (III) : R3’Z (III) ; 25 (där: R3‘ avser nägon av grupperna som definieras för R3 utom väteato-men; och Z avser en halogenatom, en C^-C*, alkansulfonyloxigrupp eller en fenylsulfonyloxigrupp) och 30 (ϋ) valbart bildas ett syraadditionssalt av föreningen med formeln : (I). II Förfarande enligt patentkrav 1 för framställning av 6-(£-klorfenyl)- 2 35 denna, kännetecknat därav, att reagenterna och reaktions- 3 ΙΗ-imidazo [ 1,2-b ] pyrazol eller farmaceutiskt acceptabla salter av 41 91871 förhällandena väljes därefter sd att R1, R3, RA och R5 är väte och R2 är β-klorfenyl.
3. Förfarande enligt patentkrav 1 för framställning av 7-fenyl-lH-5 imidazo [ 1,2-b ] pyrazol eller ett farmaceutiskt acceptable salter av denna, kännetecknat därav, att reagenterna och reaktionsförhällandena väljes därefter sä att R1 är fenyl och R2, R3, RA och R5 är väte. 10 4. Förfarande enligt patentkrav 1 för framställning av 6-(2-tienyl)-1H- imidazo [ 1,2-b ] pyrazol eller ett farmaceutiskt acceptable salter av denna, kännetecknat därav, att reagenterna och reaktions-förhällandena väljes därefter sä att R1, R3, RA och R5 är väte och R2 är 2 -tienyl. 15
5. Förfarande enligt patentkrav 1 för framställning av 7-metyl-6-(2-tienyl)-1H-imidazo [ 1,2-b ] pyrazol eller ett farmaceutiskt acceptable salter av denna, kännetecknat därav, att reagenterna och reaktionsförhällandena väljes därefter sä att R1 är metyl, R2 är 20 2-tienyl och R3, RA och R5 är väte.
6. Förfarande enligt patentkrav 1 för framställning av 6-metyl-7-fenyl-1H-imidazo [ 1,2-b ] pyrazol eller ett farmaceutiskt acceptabla salter av denna, kännetecknat därav, att reagenterna och reak- i 25 tionsförhällandena väljes därefter sä att R1 är fenyl, R2 är metyl och R3, R* och R5 är väte.
7. Förfarande enligt patentkrav 1 för framställning av 6-metyl-7-(p-klorfenyl)-1H-imidazo [ 1,2-b ] pyrazol eller ett farmaceutiskt 30 acceptabla salter av denna, kännetecknat därav, att reagenterna och reaktionsförhällandena väljes därefter sä att R1 är j>-klorfenyl, R2 är metyl och R3, RA och R5 är väte.
8. Förfarande enligt patentkrav 1 för framställning av 7-(£-metyl- 35 fenyl)-1H-imidazo [ 1,2-b ] pyrazol eller ett farmaceutiskt acceptabla 42 91871 salter av denna, kännetecknat därav, att reagenterna och reaktionsförhällandena väljes därefter sä att R1 är jj-metylfenyl och R2, R3, R4 och R5 är väte. 5 9. Förfarande enligt patentkrav 1 för framställning av 7-(2-tienyl)-1H- imidazo [ 1,2-b Jpyrazol eller ett farmaceutiskt acceptabla salter av denna, kännetecknat därav, att reagenterna och reaktionsförhällandena väljes därefter sä att R1 är 2-tienyl, R2, R3, R4 och R5 är väte. 10
10. Förfarande enligt patentkrav 1 för framställning av 6-metyl-7-(2-tienyl)-1H-imidazo [ 1,2-b ]pyrazol eller ett farmaceutiskt acceptabla salter av denna, kännetecknat därav, att reagenterna och reaktionsförhällandena väljes därefter sä att R1 är 2-tienyl, R2 är 15 metyl och R3, R4 och R5 är väte.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI935937A FI102832B (sv) | 1988-07-26 | 1993-12-30 | Mellanprodukt för framställning av som läkemedel användbara derivat av 1H-imidazo£1,2-b|pyrazol |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18613288 | 1988-07-26 | ||
| JP18613288 | 1988-07-26 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI893570A0 FI893570A0 (sv) | 1989-07-26 |
| FI893570A FI893570A (sv) | 1990-01-27 |
| FI91871B true FI91871B (sv) | 1994-05-13 |
| FI91871C FI91871C (sv) | 1994-08-25 |
Family
ID=16182931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI893570A FI91871C (sv) | 1988-07-26 | 1989-07-26 | Förfarande för framställning av som läkemedel användbara derivat av 1H-imidazo/1,2-b/pyrazol |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0353047B1 (sv) |
| JP (1) | JPH0753730B2 (sv) |
| KR (1) | KR940009785B1 (sv) |
| CN (2) | CN1032207C (sv) |
| AT (1) | ATE112569T1 (sv) |
| CA (1) | CA1340444C (sv) |
| DE (1) | DE68918651T2 (sv) |
| DK (1) | DK369289A (sv) |
| ES (1) | ES2065992T3 (sv) |
| FI (1) | FI91871C (sv) |
| HK (1) | HK1005732A1 (sv) |
| IE (1) | IE68940B1 (sv) |
| NO (1) | NO171639C (sv) |
| ZA (1) | ZA895670B (sv) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5356897A (en) * | 1991-09-09 | 1994-10-18 | Fujisawa Pharmaceutical Co., Ltd. | 3-(heteroaryl)-pyrazololi[1,5-a]pyrimidines |
| DE10019714A1 (de) | 2000-04-20 | 2002-01-10 | Gruenenthal Gmbh | Salze von bicyclischen, N-acylierten Imidazo-3-aminen und Imidazo-5-aminen |
| WO2010147898A2 (en) * | 2009-06-15 | 2010-12-23 | Rigel Pharmaceuticals, Inc. | Small molecule inhibitors of spleen tyrosine kinase (syk) |
| CN101671336B (zh) * | 2009-09-23 | 2013-11-13 | 辽宁利锋科技开发有限公司 | 芳杂环并嘧啶衍生物和类似物及其制备方法和用途 |
| AP2014007869A0 (en) * | 2012-01-25 | 2014-08-31 | Bayer Ip Gmbh | Substituted phenylimidazopyrazoles and use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2116971B (en) * | 1982-03-16 | 1985-03-27 | Erba Farmitalia | Substituted 1h-pyrazolo (1 5-a) pyrimidines and process for their preparation |
| JPH0231374B2 (ja) * | 1983-08-08 | 1990-07-12 | Fuji Photo Film Co Ltd | Harogenkaginkaraakankozairyo |
| GB8426447D0 (en) * | 1984-10-19 | 1984-11-28 | Kodak Ltd | Photographic colour couplers |
| JPS6296940A (ja) * | 1985-10-24 | 1987-05-06 | Fuji Photo Film Co Ltd | 熱現像感光材料 |
-
1989
- 1989-07-25 JP JP1191991A patent/JPH0753730B2/ja not_active Expired - Lifetime
- 1989-07-26 EP EP89307596A patent/EP0353047B1/en not_active Expired - Lifetime
- 1989-07-26 KR KR1019890010576A patent/KR940009785B1/ko not_active IP Right Cessation
- 1989-07-26 IE IE242889A patent/IE68940B1/en not_active IP Right Cessation
- 1989-07-26 FI FI893570A patent/FI91871C/sv not_active IP Right Cessation
- 1989-07-26 CN CN89107035A patent/CN1032207C/zh not_active Expired - Fee Related
- 1989-07-26 ES ES89307596T patent/ES2065992T3/es not_active Expired - Lifetime
- 1989-07-26 ZA ZA895670A patent/ZA895670B/xx unknown
- 1989-07-26 DE DE68918651T patent/DE68918651T2/de not_active Expired - Fee Related
- 1989-07-26 DK DK369289A patent/DK369289A/da not_active Application Discontinuation
- 1989-07-26 NO NO893039A patent/NO171639C/no unknown
- 1989-07-26 AT AT89307596T patent/ATE112569T1/de not_active IP Right Cessation
- 1989-07-26 CA CA000606704A patent/CA1340444C/en not_active Expired - Fee Related
-
1993
- 1993-12-10 CN CN93120938A patent/CN1034333C/zh not_active Expired - Fee Related
-
1998
- 1998-06-03 HK HK98104833A patent/HK1005732A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1340444C (en) | 1999-03-16 |
| CN1094049A (zh) | 1994-10-26 |
| DK369289D0 (da) | 1989-07-26 |
| CN1040196A (zh) | 1990-03-07 |
| EP0353047B1 (en) | 1994-10-05 |
| IE892428L (en) | 1990-01-26 |
| DK369289A (da) | 1990-01-27 |
| ATE112569T1 (de) | 1994-10-15 |
| HK1005732A1 (en) | 1999-01-22 |
| FI893570A (sv) | 1990-01-27 |
| ZA895670B (en) | 1991-03-27 |
| FI91871C (sv) | 1994-08-25 |
| NO893039L (no) | 1990-01-29 |
| KR900001701A (ko) | 1990-02-27 |
| ES2065992T3 (es) | 1995-03-01 |
| CN1032207C (zh) | 1996-07-03 |
| KR940009785B1 (ko) | 1994-10-17 |
| DE68918651T2 (de) | 1995-05-24 |
| JPH02124889A (ja) | 1990-05-14 |
| DE68918651D1 (de) | 1994-11-10 |
| CN1034333C (zh) | 1997-03-26 |
| NO171639B (no) | 1993-01-04 |
| NO893039D0 (no) | 1989-07-26 |
| EP0353047A3 (en) | 1991-07-24 |
| EP0353047A2 (en) | 1990-01-31 |
| FI893570A0 (sv) | 1989-07-26 |
| NO171639C (no) | 1993-04-14 |
| JPH0753730B2 (ja) | 1995-06-07 |
| IE68940B1 (en) | 1996-07-24 |
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| Date | Code | Title | Description |
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| BB | Publication of examined application | ||
| MM | Patent lapsed |
Owner name: SANKYO COMPANY LIMITED |