HU225162B1 - 1-[arylsulphonyl or aryl(thio)carbonyl]-pyridazin derivatives, process for producing them, pharmaceutical compositions containing them and their use - Google Patents
1-[arylsulphonyl or aryl(thio)carbonyl]-pyridazin derivatives, process for producing them, pharmaceutical compositions containing them and their use Download PDFInfo
- Publication number
- HU225162B1 HU225162B1 HU0201305A HUP0201305A HU225162B1 HU 225162 B1 HU225162 B1 HU 225162B1 HU 0201305 A HU0201305 A HU 0201305A HU P0201305 A HUP0201305 A HU P0201305A HU 225162 B1 HU225162 B1 HU 225162B1
- Authority
- HU
- Hungary
- Prior art keywords
- diazo
- hexahydro
- formula
- phenanthrene
- benzo
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 title description 2
- 125000003118 aryl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 80
- -1 cyano, carboxy Chemical group 0.000 claims description 73
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 7
- JLVWPQILIITKON-UHFFFAOYSA-N 1h-cyclohepta[c]pyridazine Chemical compound C1=CC=CC=C2NN=CC=C21 JLVWPQILIITKON-UHFFFAOYSA-N 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
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- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical group ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims 1
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- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 165
- 239000000203 mixture Substances 0.000 description 44
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
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- 238000001819 mass spectrum Methods 0.000 description 7
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- YGVDCGFUUUJCDF-UHFFFAOYSA-N 7-bromo-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(Br)=CC=C21 YGVDCGFUUUJCDF-UHFFFAOYSA-N 0.000 description 6
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- WPBQXWWFPSGWKI-UHFFFAOYSA-N 7-bromo-4-methyl-3,4-dihydro-2h-naphthalen-1-one Chemical compound BrC1=CC=C2C(C)CCC(=O)C2=C1 WPBQXWWFPSGWKI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DIYWCGZFCFYCIE-UHFFFAOYSA-N 8-bromo-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=C1C=CC=C2Br DIYWCGZFCFYCIE-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
- 239000012979 RPMI medium Substances 0.000 description 1
- 102220497176 Small vasohibin-binding protein_T47D_mutation Human genes 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 206010046793 Uterine inflammation Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 201000008275 breast carcinoma Diseases 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000037211 monthly cycles Effects 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229960004719 nandrolone Drugs 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- WZBGGLBRIYLCAB-UHFFFAOYSA-N pentaazido-lambda5-phosphane Chemical compound P(N=[N+]=[N-])(N=[N+]=[N-])(N=[N+]=[N-])(N=[N+]=[N-])N=[N+]=[N-] WZBGGLBRIYLCAB-UHFFFAOYSA-N 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000012134 supernatant fraction Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/36—Benzo-cinnolines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Gynecology & Obstetrics (AREA)
- Rheumatology (AREA)
- Pregnancy & Childbirth (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US790095P | 1995-11-06 | 1995-11-06 | |
| PCT/US1996/016227 WO1997017332A1 (en) | 1995-11-06 | 1996-10-10 | 1-arylsulphonyl, aryl(thio)carbonyl pyridazino derivatives and methods of preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP0201305A2 HUP0201305A2 (hu) | 2002-12-28 |
| HUP0201305A3 HUP0201305A3 (en) | 2003-02-28 |
| HU225162B1 true HU225162B1 (en) | 2006-07-28 |
Family
ID=21728709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0201305A HU225162B1 (en) | 1995-11-06 | 1996-10-10 | 1-[arylsulphonyl or aryl(thio)carbonyl]-pyridazin derivatives, process for producing them, pharmaceutical compositions containing them and their use |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JP2000501073A (no) |
| KR (1) | KR100360614B1 (no) |
| CN (1) | CN1110485C (no) |
| AU (1) | AU704507B2 (no) |
| BR (1) | BR9611407A (no) |
| CZ (1) | CZ286789B6 (no) |
| HU (1) | HU225162B1 (no) |
| IL (1) | IL124320A (no) |
| MX (1) | MX9803605A (no) |
| NO (1) | NO310460B1 (no) |
| NZ (1) | NZ319979A (no) |
| PL (1) | PL185618B1 (no) |
| RU (1) | RU2175969C2 (no) |
| TW (1) | TW460467B (no) |
| UA (1) | UA48989C2 (no) |
| WO (1) | WO1997017332A1 (no) |
| ZA (1) | ZA969298B (no) |
-
1996
- 1996-10-10 PL PL96326669A patent/PL185618B1/pl not_active IP Right Cessation
- 1996-10-10 JP JP9518177A patent/JP2000501073A/ja not_active Ceased
- 1996-10-10 IL IL12432096A patent/IL124320A/en not_active IP Right Cessation
- 1996-10-10 UA UA98052267A patent/UA48989C2/uk unknown
- 1996-10-10 NZ NZ319979A patent/NZ319979A/xx unknown
- 1996-10-10 RU RU98110813/04A patent/RU2175969C2/ru not_active IP Right Cessation
- 1996-10-10 WO PCT/US1996/016227 patent/WO1997017332A1/en active IP Right Grant
- 1996-10-10 CN CN96199481A patent/CN1110485C/zh not_active Expired - Fee Related
- 1996-10-10 HU HU0201305A patent/HU225162B1/hu not_active IP Right Cessation
- 1996-10-10 AU AU72637/96A patent/AU704507B2/en not_active Ceased
- 1996-10-10 KR KR10-1998-0703345A patent/KR100360614B1/ko not_active IP Right Cessation
- 1996-10-10 CZ CZ19981380A patent/CZ286789B6/cs not_active IP Right Cessation
- 1996-10-10 BR BR9611407-0A patent/BR9611407A/pt not_active Application Discontinuation
- 1996-11-05 ZA ZA9609298A patent/ZA969298B/xx unknown
- 1996-11-25 TW TW085114479A patent/TW460467B/zh not_active IP Right Cessation
-
1998
- 1998-05-05 NO NO19982030A patent/NO310460B1/no unknown
- 1998-05-06 MX MX9803605A patent/MX9803605A/es not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0201305A2 (hu) | 2002-12-28 |
| AU704507B2 (en) | 1999-04-22 |
| CN1207091A (zh) | 1999-02-03 |
| AU7263796A (en) | 1997-05-29 |
| CN1110485C (zh) | 2003-06-04 |
| NO982030L (no) | 1998-06-23 |
| KR19990067340A (ko) | 1999-08-16 |
| PL326669A1 (en) | 1998-10-12 |
| RU2175969C2 (ru) | 2001-11-20 |
| CZ138098A3 (cs) | 1998-09-16 |
| WO1997017332A1 (en) | 1997-05-15 |
| NO310460B1 (no) | 2001-07-09 |
| NO982030D0 (no) | 1998-05-05 |
| CZ286789B6 (en) | 2000-07-12 |
| TW460467B (en) | 2001-10-21 |
| BR9611407A (pt) | 1999-12-28 |
| NZ319979A (en) | 1999-11-29 |
| JP2000501073A (ja) | 2000-02-02 |
| IL124320A (en) | 2001-10-31 |
| HUP0201305A3 (en) | 2003-02-28 |
| PL185618B1 (pl) | 2003-06-30 |
| IL124320A0 (en) | 1998-12-06 |
| KR100360614B1 (ko) | 2003-06-02 |
| ZA969298B (en) | 1998-05-05 |
| MX9803605A (es) | 1998-09-30 |
| UA48989C2 (uk) | 2002-09-16 |
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| MM4A | Lapse of definitive patent protection due to non-payment of fees |