CZ298826B6 - Deriváty n-benzyl-3-indenylacetamidu pro lécbu novotvaru - Google Patents
Deriváty n-benzyl-3-indenylacetamidu pro lécbu novotvaru Download PDFInfo
- Publication number
- CZ298826B6 CZ298826B6 CZ20002157A CZ20002157A CZ298826B6 CZ 298826 B6 CZ298826 B6 CZ 298826B6 CZ 20002157 A CZ20002157 A CZ 20002157A CZ 20002157 A CZ20002157 A CZ 20002157A CZ 298826 B6 CZ298826 B6 CZ 298826B6
- Authority
- CZ
- Czechia
- Prior art keywords
- group
- alkyl
- benzyl
- indenylacetamide
- hydroxy
- Prior art date
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- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 38
- NNPSGLWEKFBPKR-UHFFFAOYSA-N n-benzyl-2-(3h-inden-1-yl)acetamide Chemical class C=1CC2=CC=CC=C2C=1CC(=O)NCC1=CC=CC=C1 NNPSGLWEKFBPKR-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 230000009826 neoplastic cell growth Effects 0.000 title claims abstract 3
- -1 heterocyclic aldehydes Chemical class 0.000 claims abstract description 98
- 238000011282 treatment Methods 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 80
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000003282 alkyl amino group Chemical group 0.000 claims description 35
- 239000003814 drug Substances 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 210000004881 tumor cell Anatomy 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims description 3
- 230000004614 tumor growth Effects 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 210000005260 human cell Anatomy 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 230000025915 regulation of apoptotic process Effects 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000005730 thiophenylene group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 abstract description 22
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- 238000000034 method Methods 0.000 description 58
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- 210000004027 cell Anatomy 0.000 description 31
- 230000000694 effects Effects 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 229940079593 drug Drugs 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 17
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- FVGRFYYBNVTYOX-UHFFFAOYSA-N 2-(1h-inden-1-yl)acetamide Chemical compound C1=CC=C2C(CC(=O)N)C=CC2=C1 FVGRFYYBNVTYOX-UHFFFAOYSA-N 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
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- 230000005764 inhibitory process Effects 0.000 description 10
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- 239000012044 organic layer Substances 0.000 description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
- 208000037062 Polyps Diseases 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 7
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/989,353 US5948779A (en) | 1997-12-12 | 1997-12-12 | Substituted condensation products of n-benzyl-3-indenyl acetamides with heterocyclic aldehydes |
| US09/206,245 US6066634A (en) | 1997-12-12 | 1998-12-07 | Substituted condensation products of N-benzyl-3-indenylacetamides heterocyclic aldehydes for neoplasia |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ20002157A3 CZ20002157A3 (cs) | 2000-10-11 |
| CZ298826B6 true CZ298826B6 (cs) | 2008-02-20 |
Family
ID=26901185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20002157A CZ298826B6 (cs) | 1997-12-12 | 1998-12-11 | Deriváty n-benzyl-3-indenylacetamidu pro lécbu novotvaru |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US6166053A (https=) |
| EP (1) | EP1044187B1 (https=) |
| JP (1) | JP4307719B2 (https=) |
| CN (1) | CN100436418C (https=) |
| AT (1) | ATE257152T1 (https=) |
| AU (1) | AU752072B2 (https=) |
| BR (1) | BR9813540A (https=) |
| CA (1) | CA2314339C (https=) |
| CZ (1) | CZ298826B6 (https=) |
| DE (1) | DE69820908T2 (https=) |
| ES (1) | ES2212383T3 (https=) |
| HU (1) | HU227153B1 (https=) |
| IL (1) | IL136603A0 (https=) |
| NO (1) | NO317097B1 (https=) |
| NZ (1) | NZ504958A (https=) |
| PL (1) | PL196936B1 (https=) |
| TR (1) | TR200001687T2 (https=) |
| WO (1) | WO1999031065A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE257152T1 (de) * | 1997-12-12 | 2004-01-15 | Osi Pharm Inc | N-benzyl-3-indenylaceamidderivative zur behandlung von neoplasia |
| IL132366A0 (en) * | 1998-10-15 | 2001-03-19 | Cell Pathways Inc | Methods for identifying compounds for inhibition of neoplastic lesions and pharmaceutical compositions containing such compounds |
| JP2004500425A (ja) * | 2000-04-19 | 2004-01-08 | リリー アイコス リミテッド ライアビリティ カンパニー | パーキンソン病の処置に対する環状ｇｍｐ特異的ホスホジエステラーゼインヒビターの使用 |
| DE10058663A1 (de) * | 2000-11-25 | 2002-05-29 | Merck Patent Gmbh | Verwendung von Thienopyrimidinen |
| WO2002067936A1 (en) * | 2001-02-21 | 2002-09-06 | Cell Pathways, Inc. | Methods for treatment of inflammatory bowel disease |
| DE10135815A1 (de) * | 2001-07-23 | 2003-02-06 | Bayer Ag | Verwendung von 2-Alkoxyphenyl-substituierten Imidazotriazinonen |
| US20030073740A1 (en) * | 2001-08-23 | 2003-04-17 | Whitehead Clark M. | Methods for treatment of lupus erythematosus |
| US20030073711A1 (en) * | 2001-08-23 | 2003-04-17 | Whitehead Clark M. | Methods for treatment of scleroderma |
| US6479493B1 (en) * | 2001-08-23 | 2002-11-12 | Cell Pathways, Inc. | Methods for treatment of type I diabetes |
| CN100398522C (zh) * | 2003-08-20 | 2008-07-02 | Irm责任有限公司 | 组织蛋白酶s的抑制剂 |
| US6995622B2 (en) * | 2004-01-09 | 2006-02-07 | Robert Bosh Gmbh | Frequency and/or phase compensated microelectromechanical oscillator |
| JP2008501407A (ja) | 2004-06-02 | 2008-01-24 | メリット ダイアモンド コーポレイション | 装身具のための快適な内側およびその内側を備える装身具 |
| CN1332930C (zh) * | 2005-08-05 | 2007-08-22 | 中国科学院上海有机化学研究所 | 制备乙氰菊酯前体的方法 |
| US8044048B2 (en) * | 2006-01-04 | 2011-10-25 | Southern Research Institute | Derivatives of sulindac, use thereof and preparation thereof |
| WO2009022756A1 (ja) * | 2007-08-13 | 2009-02-19 | Katayama Chemical Industries Co., Ltd. | 虚血性疾患の診断及び治療 |
| WO2010053910A1 (en) * | 2008-11-04 | 2010-05-14 | Wellstat Therapeutics Corporation | Synthesis of (phenylalkyloxy)phenyl-oxobutanoic acids |
| JP2013501665A (ja) | 2009-08-07 | 2013-01-17 | オークランド ユニサービシズ リミテッド | 道路から電気エネルギーを得る電気車両システム |
| US9862698B2 (en) | 2014-12-16 | 2018-01-09 | Adt Pharmaceuticals, Inc. | Indenyl compounds, pharmaceutical compositions, and medical uses thereof |
| US20160168108A1 (en) | 2014-12-16 | 2016-06-16 | Adt Pharmaceuticals, Inc. | Method of treating or preventing ras-mediated diseases |
| JP7169008B2 (ja) | 2018-04-26 | 2022-11-10 | エーディーティー ファーマシューティカルズ，エルエルシー | 抗がんインデン、インダン、アザインデン、アザインダン、医薬組成物および使用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5643959A (en) * | 1991-03-08 | 1997-07-01 | Cell Pathways, Inc. | Method for treating patients with precancerous lesions by administering substituted sulfonyl indenyl acetic and propionic acids and esters thereof |
| WO1997047303A1 (en) * | 1996-06-13 | 1997-12-18 | Cell Pathways, Inc. | Substituted benzylidene indenyl formamides, acetamides and propionamides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE257152T1 (de) * | 1997-12-12 | 2004-01-15 | Osi Pharm Inc | N-benzyl-3-indenylaceamidderivative zur behandlung von neoplasia |
| US5948779A (en) * | 1997-12-12 | 1999-09-07 | Cell Pathways, Inc. | Substituted condensation products of n-benzyl-3-indenyl acetamides with heterocyclic aldehydes |
-
1998
- 1998-12-11 AT AT98959050T patent/ATE257152T1/de not_active IP Right Cessation
- 1998-12-11 JP JP2000538992A patent/JP4307719B2/ja not_active Expired - Fee Related
- 1998-12-11 DE DE69820908T patent/DE69820908T2/de not_active Expired - Lifetime
- 1998-12-11 CA CA002314339A patent/CA2314339C/en not_active Expired - Fee Related
- 1998-12-11 CN CNB988118955A patent/CN100436418C/zh not_active Expired - Fee Related
- 1998-12-11 WO PCT/GB1998/003712 patent/WO1999031065A1/en not_active Ceased
- 1998-12-11 NZ NZ504958A patent/NZ504958A/xx unknown
- 1998-12-11 EP EP98959050A patent/EP1044187B1/en not_active Expired - Lifetime
- 1998-12-11 HU HU0100170A patent/HU227153B1/hu not_active IP Right Cessation
- 1998-12-11 IL IL13660398A patent/IL136603A0/xx active IP Right Grant
- 1998-12-11 TR TR2000/01687T patent/TR200001687T2/xx unknown
- 1998-12-11 BR BR9813540-6A patent/BR9813540A/pt not_active Application Discontinuation
- 1998-12-11 CZ CZ20002157A patent/CZ298826B6/cs not_active IP Right Cessation
- 1998-12-11 PL PL341151A patent/PL196936B1/pl not_active IP Right Cessation
- 1998-12-11 ES ES98959050T patent/ES2212383T3/es not_active Expired - Lifetime
- 1998-12-11 AU AU14981/99A patent/AU752072B2/en not_active Ceased
-
2000
- 2000-01-24 US US09/490,269 patent/US6166053A/en not_active Expired - Lifetime
- 2000-06-09 NO NO20002972A patent/NO317097B1/no not_active IP Right Cessation
- 2000-12-20 US US09/741,970 patent/US6426349B1/en not_active Expired - Fee Related
-
2002
- 2002-07-26 US US10/206,687 patent/US6610854B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5643959A (en) * | 1991-03-08 | 1997-07-01 | Cell Pathways, Inc. | Method for treating patients with precancerous lesions by administering substituted sulfonyl indenyl acetic and propionic acids and esters thereof |
| WO1997047303A1 (en) * | 1996-06-13 | 1997-12-18 | Cell Pathways, Inc. | Substituted benzylidene indenyl formamides, acetamides and propionamides |
Also Published As
| Publication number | Publication date |
|---|---|
| US6610854B2 (en) | 2003-08-26 |
| US20030009033A1 (en) | 2003-01-09 |
| US6166053A (en) | 2000-12-26 |
| EP1044187B1 (en) | 2004-01-02 |
| NO20002972L (no) | 2000-08-09 |
| AU752072B2 (en) | 2002-09-05 |
| PL196936B1 (pl) | 2008-02-29 |
| JP4307719B2 (ja) | 2009-08-05 |
| EP1044187A1 (en) | 2000-10-18 |
| IL136603A0 (en) | 2001-06-14 |
| WO1999031065A1 (en) | 1999-06-24 |
| NO317097B1 (no) | 2004-08-09 |
| PL341151A1 (en) | 2001-03-26 |
| NO20002972D0 (no) | 2000-06-09 |
| US6426349B1 (en) | 2002-07-30 |
| NZ504958A (en) | 2003-03-28 |
| CZ20002157A3 (cs) | 2000-10-11 |
| HUP0100170A3 (en) | 2001-12-28 |
| CN100436418C (zh) | 2008-11-26 |
| HUP0100170A1 (hu) | 2001-07-30 |
| DE69820908D1 (de) | 2004-02-05 |
| CA2314339A1 (en) | 1999-06-24 |
| CN1281436A (zh) | 2001-01-24 |
| AU1498199A (en) | 1999-07-05 |
| BR9813540A (pt) | 2000-10-10 |
| ATE257152T1 (de) | 2004-01-15 |
| DE69820908T2 (de) | 2004-12-23 |
| JP2002508358A (ja) | 2002-03-19 |
| HU227153B1 (en) | 2010-08-30 |
| CA2314339C (en) | 2009-09-08 |
| TR200001687T2 (tr) | 2000-10-23 |
| ES2212383T3 (es) | 2004-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20111211 |