IL123112A - History of antifungal neuroquinine and pharmaceutical preparations containing them - Google Patents
History of antifungal neuroquinine and pharmaceutical preparations containing themInfo
- Publication number
- IL123112A IL123112A IL12311296A IL12311296A IL123112A IL 123112 A IL123112 A IL 123112A IL 12311296 A IL12311296 A IL 12311296A IL 12311296 A IL12311296 A IL 12311296A IL 123112 A IL123112 A IL 123112A
- Authority
- IL
- Israel
- Prior art keywords
- cra
- substituted
- nra
- heteroaryl
- alkyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- -1 piperazino Chemical class 0.000 title description 35
- 239000002462 tachykinin receptor antagonist Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 152
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 150000003839 salts Chemical group 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 19
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 229910052702 rhenium Inorganic materials 0.000 claims abstract description 11
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 8
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 8
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- 150000001721 carbon Chemical group 0.000 claims abstract description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 229910003827 NRaRb Inorganic materials 0.000 claims abstract 2
- MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 238000006243 chemical reaction Methods 0.000 description 71
- 238000000034 method Methods 0.000 description 65
- 239000000243 solution Substances 0.000 description 63
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 44
- 238000002360 preparation method Methods 0.000 description 39
- 239000007787 solid Substances 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 28
- 239000000543 intermediate Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 108010040722 Neurokinin-2 Receptors Proteins 0.000 description 23
- 102100024304 Protachykinin-1 Human genes 0.000 description 23
- 239000003153 chemical reaction reagent Substances 0.000 description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- 239000012267 brine Substances 0.000 description 20
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
- 239000002585 base Substances 0.000 description 19
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 19
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- 230000015572 biosynthetic process Effects 0.000 description 16
- 229940125782 compound 2 Drugs 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000007792 addition Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
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- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 12
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- 239000005557 antagonist Substances 0.000 description 12
- 229940126214 compound 3 Drugs 0.000 description 12
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
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- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 9
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- BADGVUWNXHZMIU-UHFFFAOYSA-N [3-(3,4-dichlorophenyl)piperazin-1-yl]-(3,5-dimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C(=O)N2CC(NCC2)C=2C=C(Cl)C(Cl)=CC=2)=C1 BADGVUWNXHZMIU-UHFFFAOYSA-N 0.000 description 8
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- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 description 7
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Classifications
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- 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
- C07D403/12—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 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
- C07D405/02—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
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Transplantation (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US308495P | 1995-08-31 | 1995-08-31 | |
| PCT/US1996/005660 WO1996034864A1 (en) | 1995-05-02 | 1996-05-01 | Piperazino derivatives as neurokinin antagonists |
| US08/663,880 US5795894A (en) | 1995-05-02 | 1996-06-14 | Piperazino derivatives as neurokinn antagonists |
| PCT/IB1996/001018 WO1997008166A1 (en) | 1995-08-31 | 1996-08-29 | Piperazino derivatives as neurokinin antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL123112A0 IL123112A0 (en) | 1998-09-24 |
| IL123112A true IL123112A (en) | 2001-04-30 |
Family
ID=46202966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12311296A IL123112A (en) | 1995-08-31 | 1996-08-29 | History of antifungal neuroquinine and pharmaceutical preparations containing them |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0850236B1 (cs) |
| JP (2) | JP3447745B2 (cs) |
| CN (1) | CN1111529C (cs) |
| AT (1) | ATE202776T1 (cs) |
| AU (1) | AU708834B2 (cs) |
| BR (1) | BR9610277A (cs) |
| CA (1) | CA2228370C (cs) |
| CZ (1) | CZ22898A3 (cs) |
| DE (1) | DE69613705T2 (cs) |
| ES (1) | ES2158345T3 (cs) |
| GR (1) | GR3036675T3 (cs) |
| HU (1) | HUP9802552A3 (cs) |
| IL (1) | IL123112A (cs) |
| NO (1) | NO980848L (cs) |
| PL (1) | PL325339A1 (cs) |
| SK (1) | SK27498A3 (cs) |
| WO (1) | WO1997008166A1 (cs) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5892039A (en) * | 1995-08-31 | 1999-04-06 | Schering Corporation | Piperazino derivatives as neurokinin antagonists |
| US5968929A (en) * | 1996-10-30 | 1999-10-19 | Schering Corporation | Piperazino derivatives as neurokinin antagonists |
| CA2269128C (en) * | 1996-10-30 | 2005-01-11 | Schering Corporation | Piperazino derivatives as neurokinin antagonists |
| AUPO735997A0 (en) * | 1997-06-17 | 1997-07-10 | Fujisawa Pharmaceutical Co., Ltd. | Piperazine derivatives |
| UA64751C2 (uk) | 1997-06-25 | 2004-03-15 | Пфайзер Продактс Інк. | Спосіб лікування інсулінової толерантності речовинами, які посилюють секрецію гормону росту (варіанти) та фармацевтична композиція (варіанти) |
| AR014950A1 (es) * | 1998-01-14 | 2001-04-11 | Schering Corp | Derivados de piperacino antagonistas de la neuroquinina |
| ATE321042T1 (de) | 1998-12-14 | 2006-04-15 | Astellas Pharma Inc | Piperazin-derivate |
| AUPQ356899A0 (en) * | 1999-10-21 | 1999-11-11 | Fujisawa Pharmaceutical Co., Ltd. | Piperazine derivatives |
| RU2002126554A (ru) | 2000-03-06 | 2004-03-20 | Акадиа Фармасьютикалз, Инк. (Us) | Азациклические соединения для применения при лечении опосредованных серотонином заболеваний |
| TW591025B (en) * | 2000-06-13 | 2004-06-11 | Fujisawa Pharmaceutical Co | Production of the piperazine derivative |
| WO2003057698A2 (en) | 2001-12-28 | 2003-07-17 | Acadia Pharmaceuticals, Inc. | Spiroazacyclic compounds as monoamine receptor modulators |
| US6855724B2 (en) | 2002-04-08 | 2005-02-15 | Agouron Pharmaceuticals, Inc. | Tropane derivatives useful in therapy |
| US7253186B2 (en) | 2002-06-24 | 2007-08-07 | Carl-Magnus Andersson | N-substituted piperidine derivatives as serotonin receptor agents |
| US7538222B2 (en) | 2002-06-24 | 2009-05-26 | Acadia Pharmaceuticals, Inc. | N-substituted piperidine derivatives as serotonin receptor agents |
| CN100509804C (zh) | 2002-06-24 | 2009-07-08 | 阿卡蒂亚药品公司 | N-取代哌啶衍生物作为血清素受体试剂 |
| PT1587789E (pt) | 2003-01-16 | 2008-12-16 | Acadia Pharm Inc | Agonistas inversos selectivos para receptores 2a/2c da serotonina como agentes terapêuticos para doenças neurodegenerativas |
| US7820695B2 (en) | 2004-05-21 | 2010-10-26 | Acadia Pharmaceuticals, Inc. | Selective serotonin receptor inverse agonists as therapeutics for disease |
| US20050261278A1 (en) | 2004-05-21 | 2005-11-24 | Weiner David M | Selective serotonin receptor inverse agonists as therapeutics for disease |
| JP4996467B2 (ja) | 2004-09-27 | 2012-08-08 | アカディア ファーマシューティカルズ インコーポレイテッド | Ｎ−（４−フルオロベンジル）−ｎ−（１−メチルピペリジン−４−イル）−ｎ’−（４−（２−メチルプロピルオキシ）フェニルメチル）カルバミド、並びにその酒石酸塩及び結晶形態の合成 |
| US7790899B2 (en) | 2004-09-27 | 2010-09-07 | Acadia Pharmaceuticals, Inc. | Synthesis of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N′-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and crystalline forms |
| EP2117538A1 (en) | 2007-01-24 | 2009-11-18 | Glaxo Group Limited | Pharmaceutical compositions comprising 2-methoxy-5- (5-trifluoromethyl-tetrazol-i-yl-benzyl) - (2s-phenyl-piperidin-3s-yl-) |
| HRP20130713T1 (en) | 2007-03-19 | 2013-09-30 | Acadia Pharmaceuticals Inc. | Combinations of 5-ht2a inverse agonists and antagonists with antipsychotics |
| PL3325444T3 (pl) | 2015-07-20 | 2021-12-06 | Acadia Pharmaceuticals Inc. | Sposoby wytwarzania N-(4-fluorobenzylo)-N-(1-metylopiperydyn-4-ylo)-N'-(4-(2-metylopropyloksy)fenylometylo)karbamidu oraz jego soli winianowej i postaci polimorficznej C |
| WO2017165635A1 (en) | 2016-03-25 | 2017-09-28 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome p450 modulators |
| US10953000B2 (en) | 2016-03-25 | 2021-03-23 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome P450 modulators |
| EP3558311A1 (en) | 2016-12-20 | 2019-10-30 | Acadia Pharmaceuticals Inc. | Pimavanserin alone or in combination for use in the treatment of alzheimer's disease psychosis |
| WO2018200977A1 (en) | 2017-04-28 | 2018-11-01 | Acadia Pharmaceuticals Inc. | Pimavanserin for treating impulse control disorder |
| WO2019046167A1 (en) | 2017-08-30 | 2019-03-07 | Acadia Pharmaceuticals Inc. | PIMAVANSERIN FORMULATIONS |
| CN115368296A (zh) * | 2022-07-27 | 2022-11-22 | 苏州汉德创宏生化科技有限公司 | 一种n-叔丁氧羰基-4-氨基哌啶的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8908587D0 (en) * | 1989-04-15 | 1989-06-01 | Scras Societe De Conseils De R | New 2-substituted n,n'-ditrimethoxybenzoyl piperazines |
| WO1992020661A1 (en) * | 1991-05-22 | 1992-11-26 | Merck & Co., Inc. | N, n-diacylpiperazines |
| US5344830A (en) * | 1992-12-10 | 1994-09-06 | Merck & Co., Inc. | N,N-diacylpiperazine tachykinin antagonists |
| IL111730A (en) * | 1993-11-29 | 1998-12-06 | Fujisawa Pharmaceutical Co | Piperazine derivatives processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5607936A (en) * | 1994-09-30 | 1997-03-04 | Merck & Co., Inc. | Substituted aryl piperazines as neurokinin antagonists |
-
1996
- 1996-05-01 BR BR9610277A patent/BR9610277A/pt not_active Application Discontinuation
- 1996-08-29 AT AT96931188T patent/ATE202776T1/de not_active IP Right Cessation
- 1996-08-29 CZ CZ98228A patent/CZ22898A3/cs unknown
- 1996-08-29 PL PL96325339A patent/PL325339A1/xx unknown
- 1996-08-29 CA CA002228370A patent/CA2228370C/en not_active Expired - Fee Related
- 1996-08-29 HU HU9802552A patent/HUP9802552A3/hu unknown
- 1996-08-29 EP EP96931188A patent/EP0850236B1/en not_active Expired - Lifetime
- 1996-08-29 ES ES96931188T patent/ES2158345T3/es not_active Expired - Lifetime
- 1996-08-29 IL IL12311296A patent/IL123112A/en not_active IP Right Cessation
- 1996-08-29 WO PCT/IB1996/001018 patent/WO1997008166A1/en not_active Ceased
- 1996-08-29 SK SK274-98A patent/SK27498A3/sk unknown
- 1996-08-29 CN CN96197720A patent/CN1111529C/zh not_active Expired - Fee Related
- 1996-08-29 JP JP51006997A patent/JP3447745B2/ja not_active Expired - Lifetime
- 1996-08-29 AU AU69979/96A patent/AU708834B2/en not_active Ceased
- 1996-08-29 DE DE69613705T patent/DE69613705T2/de not_active Expired - Lifetime
-
1998
- 1998-02-27 NO NO980848A patent/NO980848L/no not_active Application Discontinuation
-
2000
- 2000-05-24 JP JP2000153870A patent/JP3315970B2/ja not_active Expired - Fee Related
-
2001
- 2001-09-20 GR GR20010401532T patent/GR3036675T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9802552A2 (hu) | 1999-10-28 |
| WO1997008166A1 (en) | 1997-03-06 |
| IL123112A0 (en) | 1998-09-24 |
| CA2228370C (en) | 2002-10-01 |
| AU708834B2 (en) | 1999-08-12 |
| SK27498A3 (en) | 1998-12-02 |
| DE69613705D1 (de) | 2001-08-09 |
| DE69613705T2 (de) | 2002-05-16 |
| CN1200120A (zh) | 1998-11-25 |
| JP3447745B2 (ja) | 2003-09-16 |
| JP3315970B2 (ja) | 2002-08-19 |
| GR3036675T3 (en) | 2001-12-31 |
| BR9610277A (pt) | 1999-07-06 |
| CN1111529C (zh) | 2003-06-18 |
| JPH10511105A (ja) | 1998-10-27 |
| PL325339A1 (en) | 1998-07-20 |
| ES2158345T3 (es) | 2001-09-01 |
| EP0850236A1 (en) | 1998-07-01 |
| EP0850236B1 (en) | 2001-07-04 |
| NO980848L (no) | 1998-04-30 |
| ATE202776T1 (de) | 2001-07-15 |
| JP2000344766A (ja) | 2000-12-12 |
| HUP9802552A3 (en) | 1999-11-29 |
| AU6997996A (en) | 1997-03-19 |
| NO980848D0 (no) | 1998-02-27 |
| CZ22898A3 (cs) | 1998-07-15 |
| CA2228370A1 (en) | 1997-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |