NO320322B1 - Forbindelse, fremgangsmate for fremstilling av denne, legemiddel og farmasoytisk preparat inneholdende denne, anvendelse av forbindelsen og fremgangsmate for fremstilling av et legemiddel. - Google Patents
Forbindelse, fremgangsmate for fremstilling av denne, legemiddel og farmasoytisk preparat inneholdende denne, anvendelse av forbindelsen og fremgangsmate for fremstilling av et legemiddel. Download PDFInfo
- Publication number
- NO320322B1 NO320322B1 NO19971116A NO971116A NO320322B1 NO 320322 B1 NO320322 B1 NO 320322B1 NO 19971116 A NO19971116 A NO 19971116A NO 971116 A NO971116 A NO 971116A NO 320322 B1 NO320322 B1 NO 320322B1
- Authority
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- Norway
- Prior art keywords
- compound
- formula
- stands
- alkyl
- glycosyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 50
- 239000003814 drug Substances 0.000 title claims description 19
- 229940079593 drug Drugs 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 methoxy, carboxy, methyloxycarbonyl Chemical group 0.000 claims abstract description 17
- 125000003147 glycosyl group Chemical group 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 239000013543 active substance Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 230000004071 biological effect Effects 0.000 claims abstract description 4
- 150000004676 glycans Polymers 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 150000002482 oligosaccharides Polymers 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims abstract description 3
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- 229940124530 sulfonamide Drugs 0.000 claims abstract description 3
- 239000004480 active ingredient Substances 0.000 claims description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
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- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 201000003068 rheumatic fever Diseases 0.000 claims description 3
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
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- 230000000996 additive effect Effects 0.000 claims description 2
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- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims description 2
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 abstract 1
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- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 description 38
- 239000000651 prodrug Substances 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 150000004702 methyl esters Chemical class 0.000 description 17
- 229940088598 enzyme Drugs 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 102000004190 Enzymes Human genes 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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- 239000000126 substance Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 8
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- 229910002027 silica gel Inorganic materials 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 230000004913 activation Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 6
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 6
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
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- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96103866 | 1996-03-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO971116D0 NO971116D0 (no) | 1997-03-11 |
| NO971116L NO971116L (no) | 1997-09-15 |
| NO320322B1 true NO320322B1 (no) | 2005-11-21 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19971116A NO320322B1 (no) | 1996-03-12 | 1997-03-11 | Forbindelse, fremgangsmate for fremstilling av denne, legemiddel og farmasoytisk preparat inneholdende denne, anvendelse av forbindelsen og fremgangsmate for fremstilling av et legemiddel. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5935995A (ro) |
| EP (1) | EP0795334B1 (ro) |
| JP (1) | JP4392065B2 (ro) |
| KR (1) | KR100466467B1 (ro) |
| CN (1) | CN1168733C (ro) |
| AT (1) | ATE316799T1 (ro) |
| AU (1) | AU708202B2 (ro) |
| BG (1) | BG61900B1 (ro) |
| BR (1) | BRPI9701248B1 (ro) |
| CA (1) | CA2199664C (ro) |
| CZ (1) | CZ297994B6 (ro) |
| DE (1) | DE59712561D1 (ro) |
| DK (1) | DK0795334T3 (ro) |
| ES (1) | ES2257756T3 (ro) |
| HU (1) | HU228764B1 (ro) |
| NO (1) | NO320322B1 (ro) |
| NZ (1) | NZ314368A (ro) |
| PL (1) | PL189604B1 (ro) |
| RO (1) | RO120951B1 (ro) |
| RU (1) | RU2191021C2 (ro) |
| SG (1) | SG50011A1 (ro) |
| SI (1) | SI0795334T1 (ro) |
| TR (1) | TR199700178A2 (ro) |
| UA (1) | UA50719C2 (ro) |
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| US5525606A (en) | 1994-08-01 | 1996-06-11 | The United States Of America As Represented By The Department Of Health And Human Services | Substituted 06-benzylguanines and 6(4)-benzyloxypyrimidines |
| DE19720312A1 (de) * | 1997-05-15 | 1998-11-19 | Hoechst Ag | Zubereitung mit erhöhter in vivo Verträglichkeit |
| AU772153B2 (en) | 1999-02-12 | 2004-04-08 | Molecular Insight Pharmaceuticals, Inc. | Matrices for drug delivery and methods for making and using the same |
| US6716452B1 (en) * | 2000-08-22 | 2004-04-06 | New River Pharmaceuticals Inc. | Active agent delivery systems and methods for protecting and administering active agents |
| PT1175433E (pt) | 1999-05-04 | 2005-11-30 | Strakan Int Ltd | Glicosidos androgenos e sua actividade androgenica |
| US6191119B1 (en) * | 1999-10-15 | 2001-02-20 | Supergen, Inc. | Combination therapy including 9-nitro-20(S)-camptothecin |
| US8394813B2 (en) | 2000-11-14 | 2013-03-12 | Shire Llc | Active agent delivery systems and methods for protecting and administering active agents |
| DE10058596A1 (de) * | 2000-11-25 | 2002-06-06 | Aventis Pharma Gmbh | Verfahren zum Screening von chemischen Verbindungen zur Modulierung der Wechselwirkung einer EVH1-Domäne oder eines Proteins mit einer EVH1-Domäne mit einer EVH1-Bindedomäne oder einem Protein mit einer EVH1-Bindedomäne sowie ein Verfahren zum Nachweis besagter Wechselwirkung |
| US20060014697A1 (en) | 2001-08-22 | 2006-01-19 | Travis Mickle | Pharmaceutical compositions for prevention of overdose or abuse |
| US7169752B2 (en) | 2003-09-30 | 2007-01-30 | New River Pharmaceuticals Inc. | Compounds and compositions for prevention of overdose of oxycodone |
| AU2002323570A1 (en) | 2001-08-30 | 2003-03-10 | Chemocentryx, Inc. | Bicyclic compounds as inhibitors of chemokine binding to us28 |
| US20050203061A1 (en) * | 2002-06-20 | 2005-09-15 | Shinya Yamashita | Prodrug, medicinal utilization thereof and process for producing the same |
| US8133881B2 (en) | 2003-01-13 | 2012-03-13 | Shire Llc | Carbohydrate conjugates to prevent abuse of controlled substances |
| US7160867B2 (en) * | 2003-05-16 | 2007-01-09 | Isotechnika, Inc. | Rapamycin carbohydrate derivatives |
| JP2007530664A (ja) * | 2004-03-30 | 2007-11-01 | ペインセプター ファーマ コーポレーション | ゲートイオンチャンネルを調節するための組成物及び方法 |
| US7825096B2 (en) * | 2004-09-08 | 2010-11-02 | The United States Of America As Represented By The Department Of Health And Human Services | O6-alkylguanine-DNA alkyltransferase inactivators and beta-glucuronidase cleavable prodrugs |
| RU2527531C2 (ru) * | 2007-04-06 | 2014-09-10 | Зайофарм Онколоджи, Инк. | Соли изофосфорамидного иприта и его аналогов |
| GB0907551D0 (en) * | 2009-05-01 | 2009-06-10 | Univ Dundee | Treatment or prophylaxis of proliferative conditions |
| MX336332B (es) * | 2009-09-02 | 2016-01-15 | Auckland Uniservices Ltd | Inhibidores de cinasa, formas de profarmaco de los mismos y su uso en terapia. |
| KR101253399B1 (ko) | 2010-10-26 | 2013-04-11 | 영남대학교 산학협력단 | 아포지단백질 ａ－ｉ 및 그 변이체를 포함한 재조합 고밀도지단백질을 이용한 라파마이신 제형 |
| KR101628872B1 (ko) | 2014-05-28 | 2016-06-09 | 주식회사 레고켐 바이오사이언스 | 자가-희생 기를 포함하는 화합물 |
| CA3006247A1 (en) | 2015-11-25 | 2017-06-01 | Legochem Biosciences, Inc. | Conjugates comprising peptide groups and methods related thereto |
| EP3380126A4 (en) | 2015-11-25 | 2019-07-24 | LegoChem Biosciences, Inc. | ANTIBODY-MEDICINAL CONJUGATES COMPRISING BRANCHED LINKS AND RELATED METHODS |
| US11413353B2 (en) | 2015-11-25 | 2022-08-16 | Legochem Biosciences, Inc. | Conjugates comprising self-immolative groups and methods related thereto |
| US11229708B2 (en) | 2015-12-04 | 2022-01-25 | Seagen Inc. | Conjugates of quaternized tubulysin compounds |
| US11793880B2 (en) | 2015-12-04 | 2023-10-24 | Seagen Inc. | Conjugates of quaternized tubulysin compounds |
| CA3058360A1 (en) | 2017-03-29 | 2018-10-04 | Legochem Biosciences, Inc. | Pyrrolobenzodiazepine dimer prodrug and ligand-linker conjugate compound of the same |
| CA3091027A1 (en) | 2018-02-02 | 2019-08-08 | Maverix Oncology, Inc. | Small molecule drug conjugates of gemcitabine monophosphate |
| MX2020011554A (es) | 2018-05-09 | 2020-11-24 | Legochem Biosciences Inc | Composiciones y metodos relacionados con conjugados de farmacos de anticuerpo anti grupo de diferenciacion 19 (cd19). |
| KR20210028544A (ko) | 2019-09-04 | 2021-03-12 | 주식회사 레고켐 바이오사이언스 | 인간 ror1에 대한 항체를 포함하는 항체 약물 접합체 및 이의 용도 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5284856A (en) * | 1988-10-28 | 1994-02-08 | Hoechst Aktiengesellschaft | Oncogene-encoded kinases inhibition using 4-H-1-benzopyran-4-one derivatives |
| DE3836676A1 (de) * | 1988-10-28 | 1990-05-03 | Hoechst Ag | Die verwendung von 4h-1-benzopyran-4-on-derivaten, neue 4h-1-benzopyran-4-on-derivate und diese enthaltende arzneimittel |
| WO1990007929A1 (en) * | 1989-01-23 | 1990-07-26 | Akzo N.V. | Site specific in-vivo activation of therapeutic drugs |
| DE4106389A1 (de) * | 1991-02-28 | 1992-09-03 | Behringwerke Ag | Fusionsproteine zur prodrug-aktivierung, ihre herstellung und verwendung |
| US5494911A (en) * | 1990-05-18 | 1996-02-27 | Hoechst Aktiengesellschaft | Isoxazole-4-carboxamides and hydroxyalkylidenecyanoacetamides, pharmaceuticals containing these compounds and their use |
| FR2676058B1 (fr) * | 1991-04-30 | 1994-02-25 | Hoechst Lab | Prodrogues glycosylees, leur procede de preparation et leur utilisation dans le traitement des cancers. |
| EP0538799B1 (en) * | 1991-10-25 | 1995-03-15 | TUNGSRAM Részvénytársaság | Single-capped low-pressure discharge lamp |
| DE4233152A1 (de) * | 1992-10-02 | 1994-04-07 | Behringwerke Ag | Antikörper-Enzym-Konjugate zur Prodrug-Aktivierung |
| CA2081281A1 (en) * | 1992-10-23 | 1994-04-24 | Shing-Ming Wang | Activation of glucuronide prodrugs by ligand-beta-glucuronidase conjugates for chemotherapy |
| DE4236237A1 (de) * | 1992-10-27 | 1994-04-28 | Behringwerke Ag | Prodrugs, ihre Herstellung und Verwendung als Arzneimittel |
| DE4314556A1 (de) * | 1993-05-04 | 1994-11-10 | Behringwerke Ag | Modifizierte Antikörperenzymkonjugate und Fusionsproteine sowie ihre Anwendung zur tumorselektiven Therapie |
| EP0647450A1 (en) * | 1993-09-09 | 1995-04-12 | BEHRINGWERKE Aktiengesellschaft | Improved prodrugs for enzyme mediated activation |
| DE4417865A1 (de) * | 1994-05-20 | 1995-11-23 | Behringwerke Ag | Kombination von Tumornekrose-induzierenden Substanzen mit Substanzen, die durch Nekrosen aktiviert werden, zur selektiven Tumortherapie |
-
1997
- 1997-02-27 EP EP97103162A patent/EP0795334B1/de not_active Expired - Lifetime
- 1997-02-27 SI SI9730727T patent/SI0795334T1/sl unknown
- 1997-02-27 AT AT97103162T patent/ATE316799T1/de active
- 1997-02-27 DE DE59712561T patent/DE59712561D1/de not_active Expired - Lifetime
- 1997-02-27 DK DK97103162T patent/DK0795334T3/da active
- 1997-02-27 ES ES97103162T patent/ES2257756T3/es not_active Expired - Lifetime
- 1997-03-03 RO RO97-00402A patent/RO120951B1/ro unknown
- 1997-03-06 RU RU97103585/14A patent/RU2191021C2/ru not_active IP Right Cessation
- 1997-03-06 BG BG101290A patent/BG61900B1/bg unknown
- 1997-03-07 AU AU16205/97A patent/AU708202B2/en not_active Ceased
- 1997-03-10 TR TR97/00178A patent/TR199700178A2/xx unknown
- 1997-03-10 NZ NZ314368A patent/NZ314368A/xx not_active IP Right Cessation
- 1997-03-10 PL PL97318878A patent/PL189604B1/pl unknown
- 1997-03-11 UA UA97031095A patent/UA50719C2/uk unknown
- 1997-03-11 CZ CZ0074297A patent/CZ297994B6/cs not_active IP Right Cessation
- 1997-03-11 CN CNB971034656A patent/CN1168733C/zh not_active Expired - Fee Related
- 1997-03-11 NO NO19971116A patent/NO320322B1/no not_active IP Right Cessation
- 1997-03-11 US US08/814,655 patent/US5935995A/en not_active Expired - Lifetime
- 1997-03-11 CA CA002199664A patent/CA2199664C/en not_active Expired - Fee Related
- 1997-03-11 BR BRPI9701248A patent/BRPI9701248B1/pt not_active IP Right Cessation
- 1997-03-11 JP JP05598397A patent/JP4392065B2/ja not_active Expired - Fee Related
- 1997-03-12 HU HU9700579A patent/HU228764B1/hu not_active IP Right Cessation
- 1997-03-12 SG SG1997000702A patent/SG50011A1/en unknown
- 1997-03-12 KR KR1019970008174A patent/KR100466467B1/ko not_active IP Right Cessation
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