DE69620458T2 - Benzofuran-carboxamide und -sulfonamide - Google Patents
Benzofuran-carboxamide und -sulfonamideInfo
- Publication number
- DE69620458T2 DE69620458T2 DE69620458T DE69620458T DE69620458T2 DE 69620458 T2 DE69620458 T2 DE 69620458T2 DE 69620458 T DE69620458 T DE 69620458T DE 69620458 T DE69620458 T DE 69620458T DE 69620458 T2 DE69620458 T2 DE 69620458T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- methoxy
- benzofuransulfonamide
- disease
- heteroarylalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- -1 BENZOFURANE CARBOXAMIDES Chemical class 0.000 title claims description 29
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
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- DKLCYCSRYCEYAU-UHFFFAOYSA-N 2-ethyl-7-methoxy-n-(pyridin-3-ylmethyl)-1-benzofuran-4-sulfonamide Chemical compound C1=CC(OC)=C2OC(CC)=CC2=C1S(=O)(=O)NCC1=CC=CN=C1 DKLCYCSRYCEYAU-UHFFFAOYSA-N 0.000 claims description 2
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- AHGCKRVJQYBCRZ-UHFFFAOYSA-N n-benzyl-2-ethyl-7-methoxy-1-benzofuran-4-sulfonamide Chemical compound C1=CC(OC)=C2OC(CC)=CC2=C1S(=O)(=O)NCC1=CC=CC=C1 AHGCKRVJQYBCRZ-UHFFFAOYSA-N 0.000 claims description 2
- RTMNIUUBYBNFHX-UHFFFAOYSA-N n-benzyl-2-ethyl-7-methoxy-n-(pyridin-2-ylmethyl)-1-benzofuran-4-sulfonamide Chemical compound C1=CC(OC)=C2OC(CC)=CC2=C1S(=O)(=O)N(CC=1N=CC=CC=1)CC1=CC=CC=C1 RTMNIUUBYBNFHX-UHFFFAOYSA-N 0.000 claims description 2
- SCACIMJYGFQKOY-UHFFFAOYSA-N n-benzyl-2-ethyl-7-methoxy-n-methylsulfonyl-1-benzofuran-4-sulfonamide Chemical compound C1=CC(OC)=C2OC(CC)=CC2=C1S(=O)(=O)N(S(C)(=O)=O)CC1=CC=CC=C1 SCACIMJYGFQKOY-UHFFFAOYSA-N 0.000 claims description 2
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- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
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- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
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- 230000002335 preservative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 210000001044 sensory neuron Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
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- 239000001593 sorbitan monooleate Substances 0.000 description 1
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- 239000008107 starch Substances 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000008009 topical excipient Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
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- 230000009385 viral infection Effects 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
-
- 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
- A61P11/06—Antiasthmatics
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D405/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9524832.4A GB9524832D0 (en) | 1995-12-05 | 1995-12-05 | Novel compounds |
| GBGB9610515.0A GB9610515D0 (en) | 1996-05-20 | 1996-05-20 | Novel compounds |
| GBGB9610712.3A GB9610712D0 (en) | 1995-12-05 | 1996-05-22 | Novel compounds |
| PCT/GB1996/003012 WO1997020833A1 (en) | 1995-12-05 | 1996-12-05 | Benzofuran carboxamides and sulphonamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69620458D1 DE69620458D1 (de) | 2002-05-08 |
| DE69620458T2 true DE69620458T2 (de) | 2002-10-02 |
Family
ID=27268015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69620458T Expired - Fee Related DE69620458T2 (de) | 1995-12-05 | 1996-12-05 | Benzofuran-carboxamide und -sulfonamide |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5773467A (enExample) |
| EP (1) | EP0873331B1 (enExample) |
| JP (1) | JP2000501411A (enExample) |
| KR (1) | KR19990071894A (enExample) |
| CN (1) | CN1100773C (enExample) |
| AT (1) | ATE215540T1 (enExample) |
| AU (1) | AU697976B2 (enExample) |
| BR (1) | BR9611897A (enExample) |
| CA (1) | CA2238376C (enExample) |
| CZ (1) | CZ292443B6 (enExample) |
| DE (1) | DE69620458T2 (enExample) |
| ES (1) | ES2172695T3 (enExample) |
| HU (1) | HUP9903797A3 (enExample) |
| NO (1) | NO982570L (enExample) |
| PL (1) | PL327181A1 (enExample) |
| WO (1) | WO1997020833A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK282676B6 (sk) * | 1996-05-20 | 2002-11-06 | Darwin Discovery Limited | Benzofuránové karboxamidy a tioamidy, farmaceutický prípravok s ich obsahom a ich použitie |
| EP0923568B9 (en) * | 1996-08-19 | 2003-08-13 | ALTANA Pharma AG | Novel benzofuran-4-carboxamides |
| JP3268236B2 (ja) | 1997-07-22 | 2002-03-25 | シャープ株式会社 | 電子写真感光体、及びビスヒドラゾン化合物およびその中間体、ならびにそれら化合物の製造方法 |
| AU9281198A (en) | 1997-10-01 | 1999-04-23 | Kyowa Hakko Kogyo Co. Ltd. | Benzofuran derivatives |
| WO1999037640A1 (en) * | 1998-01-26 | 1999-07-29 | Kyowa Hakko Kogyo Co., Ltd. | Oxygenic heterocyclic compounds |
| WO1999040085A1 (en) * | 1998-02-09 | 1999-08-12 | Darwin Discovery Limited | Benzofuran-4-carboxamides and their therapeutic use |
| FR2778662B1 (fr) * | 1998-05-12 | 2000-06-16 | Adir | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| TW555759B (en) * | 1998-06-08 | 2003-10-01 | Darwin Discovery Ltd | Heterocyclic compounds and their therapeutic use |
| WO1999064414A1 (de) * | 1998-06-10 | 1999-12-16 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Benzamide mit tetrahydrofuranyloxy-substituenten als inhibitoren der phosphodiesterase 4 |
| PT1212089E (pt) | 1999-08-21 | 2006-08-31 | Altana Pharma Ag | Combinacao sinergica de roflumilast e salmeterol |
| US7217722B2 (en) * | 2000-02-01 | 2007-05-15 | Kirin Beer Kabushiki Kaisha | Nitrogen-containing compounds having kinase inhibitory activity and drugs containing the same |
| GB0011802D0 (en) * | 2000-05-16 | 2000-07-05 | Smithkline Beecham | Method for enhancing cognitive function |
| KR20050115331A (ko) | 2003-04-01 | 2005-12-07 | 어플라이드 리서치 시스템스 에이알에스 홀딩 엔.브이. | 불임증 포스포디에스터라제의 억제제 |
| FR2903106B1 (fr) * | 2006-07-03 | 2010-07-30 | Sanofi Aventis | Utilisations de 2-benzoyl-imidazopyridines en therapeutique |
| EP2196465A1 (en) | 2008-12-15 | 2010-06-16 | Almirall, S.A. | (3-oxo)pyridazin-4-ylurea derivatives as PDE4 inhibitors |
| AR074760A1 (es) * | 2008-12-18 | 2011-02-09 | Metabolex Inc | Agonistas del receptor gpr120 y usos de los mismos en medicamentos para el tratamiento de diabetes y el sindrome metabolico. |
| EP2226323A1 (en) | 2009-02-27 | 2010-09-08 | Almirall, S.A. | New tetrahydropyrazolo[3,4-c]isoquinolin-5-amine derivatives |
| EP2380890A1 (en) | 2010-04-23 | 2011-10-26 | Almirall, S.A. | New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 inhibitors |
| EP2394998A1 (en) | 2010-05-31 | 2011-12-14 | Almirall, S.A. | 3-(5-Amino-6-oxo-1,6-dihydropyridazin-3-yl)-biphenyl derivatives as PDE4 inhibitors |
| EP2597093B1 (en) | 2010-07-22 | 2014-11-05 | Fuso Pharmaceutical Industries, Ltd. | Benzofuranone compound and pharmaceutical composition containing same |
| EP3242661B1 (en) | 2015-01-05 | 2019-08-21 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Myc g-quadruplex stabilizing small molecules and their use |
| CN114149457B (zh) * | 2021-11-03 | 2024-04-12 | 湖北民族大学 | 一种苯并[c][1,2]氧杂硼戊环-1(3H)-醇类合物及其用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8705871A1 (es) * | 1984-12-29 | 1987-05-16 | Kaken Pharma Co Ltd | Un procedimiento para preparar un derivado de benzofurano |
| EP0685475B1 (en) * | 1994-05-31 | 1999-01-13 | Bayer Ag | Amino-benzofuryl-and thienyl-derivatives |
| DE59508773D1 (de) * | 1994-07-22 | 2000-11-09 | Byk Gulden Lomberg Chem Fab | Dihydrobenzofurane |
| PT771794E (pt) * | 1995-05-19 | 2006-09-29 | Kyowa Hakko Kogyo Kk | Compostos heterociclicos contendo oxigenio |
| SK282676B6 (sk) * | 1996-05-20 | 2002-11-06 | Darwin Discovery Limited | Benzofuránové karboxamidy a tioamidy, farmaceutický prípravok s ich obsahom a ich použitie |
-
1996
- 1996-12-05 KR KR1019980704179A patent/KR19990071894A/ko not_active Ceased
- 1996-12-05 BR BR9611897-0A patent/BR9611897A/pt active Search and Examination
- 1996-12-05 DE DE69620458T patent/DE69620458T2/de not_active Expired - Fee Related
- 1996-12-05 CZ CZ19981714A patent/CZ292443B6/cs not_active IP Right Cessation
- 1996-12-05 AT AT96941138T patent/ATE215540T1/de not_active IP Right Cessation
- 1996-12-05 CA CA002238376A patent/CA2238376C/en not_active Expired - Fee Related
- 1996-12-05 WO PCT/GB1996/003012 patent/WO1997020833A1/en not_active Ceased
- 1996-12-05 US US08/761,102 patent/US5773467A/en not_active Expired - Fee Related
- 1996-12-05 PL PL96327181A patent/PL327181A1/xx unknown
- 1996-12-05 HU HU9903797A patent/HUP9903797A3/hu unknown
- 1996-12-05 JP JP9521090A patent/JP2000501411A/ja not_active Ceased
- 1996-12-05 EP EP96941138A patent/EP0873331B1/en not_active Expired - Lifetime
- 1996-12-05 ES ES96941138T patent/ES2172695T3/es not_active Expired - Lifetime
- 1996-12-05 CN CN96198844A patent/CN1100773C/zh not_active Expired - Fee Related
- 1996-12-05 AU AU10386/97A patent/AU697976B2/en not_active Ceased
-
1998
- 1998-06-04 NO NO982570A patent/NO982570L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0873331A1 (en) | 1998-10-28 |
| CA2238376A1 (en) | 1997-06-12 |
| DE69620458D1 (de) | 2002-05-08 |
| CZ171498A3 (cs) | 1998-10-14 |
| BR9611897A (pt) | 1999-12-28 |
| HUP9903797A3 (en) | 2001-08-28 |
| MX9804466A (es) | 1998-12-31 |
| CN1100773C (zh) | 2003-02-05 |
| CZ292443B6 (cs) | 2003-09-17 |
| US5773467A (en) | 1998-06-30 |
| AU697976B2 (en) | 1998-10-22 |
| ATE215540T1 (de) | 2002-04-15 |
| CN1208411A (zh) | 1999-02-17 |
| EP0873331B1 (en) | 2002-04-03 |
| JP2000501411A (ja) | 2000-02-08 |
| NO982570D0 (no) | 1998-06-04 |
| HUP9903797A2 (hu) | 2001-04-28 |
| CA2238376C (en) | 2006-08-15 |
| PL327181A1 (en) | 1998-11-23 |
| ES2172695T3 (es) | 2002-10-01 |
| AU1038697A (en) | 1997-06-27 |
| WO1997020833A1 (en) | 1997-06-12 |
| KR19990071894A (ko) | 1999-09-27 |
| NO982570L (no) | 1998-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |