RU98116122A - SELECTIVELY ACTING TAXANS, METHOD FOR PRODUCING THEM AND THEIR USE AS MEDICINES - Google Patents
SELECTIVELY ACTING TAXANS, METHOD FOR PRODUCING THEM AND THEIR USE AS MEDICINESInfo
- Publication number
- RU98116122A RU98116122A RU98116122/04A RU98116122A RU98116122A RU 98116122 A RU98116122 A RU 98116122A RU 98116122/04 A RU98116122/04 A RU 98116122/04A RU 98116122 A RU98116122 A RU 98116122A RU 98116122 A RU98116122 A RU 98116122A
- Authority
- RU
- Russia
- Prior art keywords
- general formula
- esterification
- desphenyl
- debenzoyl
- pyridyl
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000005886 esterification reaction Methods 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 229940079593 drugs Drugs 0.000 claims 3
- 229920000858 Cyclodextrin Polymers 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000000027 (C1-C10) alkoxy group Chemical class 0.000 claims 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims 1
- 229940045698 antineoplastic Taxanes Drugs 0.000 claims 1
- 229960004853 betadex Drugs 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002502 liposome Substances 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N α-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N β-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims 1
- GDSRMADSINPKSL-HSEONFRVSA-N γ-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims 1
- 0 CCC(*)(C(C(C(C(C(C)=O)I)c1ccncc1)O)=O)O Chemical compound CCC(*)(C(C(C(C(C(C)=O)I)c1ccncc1)O)=O)O 0.000 description 1
Claims (9)
где Sk может представлять собой
R1 может представлять собой водород или C1-C10ацил, R2 может представлять собой α-OH, R3 может представлять собой C1-C10алкил, X-замещенный фенил, C1-C10алкокси, X может представлять собой водород, галоген, -N3 или -CN, и свободные гидроксигруппы в I могут быть далее функционально модифицированы путем этерификации, эстерификации а также их α-, β- и γ-циклодекстриновые клатраты, а также соединения общей формулы I, заключенные в липосомы.1. Taxanes of general formula 1 with pharmacological activity
where Sk can be
R 1 may be hydrogen or C 1 -C 10 acyl, R 2 may be α-OH, R 3 may be C 1 -C 10 alkyl, X-substituted phenyl, C 1 -C 10 alkoxy, X may be hydrogen, halogen, -N 3 or -CN, and the free hydroxy groups in I can be further functionally modified by esterification, esterification, as well as their α-, β- and γ-cyclodextrin clathrates, as well as compounds of general formula I enclosed in liposomes .
где R1 и R2 определены здесь выше, и гидроксигруппы, содержащиеся в II, необязательно защищены,
взаимодействует с соединением общей формулы IIIа, IIIb или IIIс,
где R3 определен здесь выше, и X' может представлять собой гидрокси, O-алкил или галоген, и где свободные гидроксигруппы защищены путем этерификации или эстерификации, с получением соединений общей формулы I, в которых свободные гидроксигруппы могут быть далее функционально модифицированы путем этерификации или эстерификации.6. The method of obtaining taxane derivatives of General formula 1 according to claims 1-5, characterized in that the alcohol has the general formula II
where R 1 and R 2 are defined hereinabove and the hydroxy groups contained in II are optionally protected,
interacts with a compound of the general formula IIIa, IIIb or IIIc,
where R 3 is defined hereinbefore and X 'may be hydroxy, O-alkyl or halogen, and where free hydroxy groups are protected by esterification or esterification to give compounds of general formula I in which free hydroxy groups can be further functionally modified by esterification or esterification.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19605024A DE19605024A1 (en) | 1996-01-31 | 1996-01-31 | New selective taxanes, processes for their preparation and their pharmaceutical use |
| DE19605024.3 | 1996-01-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98116122A true RU98116122A (en) | 2000-06-27 |
| RU2163599C2 RU2163599C2 (en) | 2001-02-27 |
Family
ID=7785142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98116122/04A RU2163599C2 (en) | 1996-01-31 | 1997-01-31 | Taxanes, method of their synthesis and drug based on thereof |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6162920A (en) |
| EP (1) | EP0896577B1 (en) |
| JP (1) | JP2001505527A (en) |
| KR (1) | KR19990082151A (en) |
| CN (1) | CN1073108C (en) |
| AT (1) | ATE233757T1 (en) |
| AU (1) | AU714313B2 (en) |
| BR (1) | BR9708295A (en) |
| CA (1) | CA2244746A1 (en) |
| CZ (1) | CZ292504B6 (en) |
| DE (2) | DE19605024A1 (en) |
| DK (1) | DK0896577T3 (en) |
| ES (1) | ES2192261T3 (en) |
| HK (1) | HK1018778A1 (en) |
| HU (1) | HUP9901027A3 (en) |
| IL (1) | IL124951A (en) |
| NO (1) | NO983509D0 (en) |
| PL (1) | PL186796B1 (en) |
| PT (1) | PT896577E (en) |
| RU (1) | RU2163599C2 (en) |
| SK (1) | SK101198A3 (en) |
| TR (1) | TR199801415T2 (en) |
| TW (1) | TW444015B (en) |
| UA (1) | UA49007C2 (en) |
| WO (1) | WO1997028156A1 (en) |
| ZA (1) | ZA97847B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8658203B2 (en) | 2004-05-03 | 2014-02-25 | Merrimack Pharmaceuticals, Inc. | Liposomes useful for drug delivery to the brain |
| US8703181B2 (en) | 2004-05-03 | 2014-04-22 | Merrimack Pharmaceuticals, Inc. | Liposomes useful for drug delivery |
| US10456360B2 (en) | 2015-10-16 | 2019-10-29 | Ipsen Biopharm Ltd. | Stabilizing camptothecin pharmaceutical compositions |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002070512A1 (en) | 2001-03-07 | 2002-09-12 | Daiichi Pharmaceutical Co, Ltd. | Method for producing 2-azetidinone derivative |
| EP1605866B1 (en) | 2003-03-03 | 2016-07-06 | Syntach AG | Electrical conduction block implant device |
| CN1296391C (en) * | 2004-03-04 | 2007-01-24 | 中国人民解放军第二军医大学 | Compound of fluorinated carboxy alkyl cyclic starch gun ester kind and preparation process and application thereof |
| AU2013202947B2 (en) | 2012-06-13 | 2016-06-02 | Ipsen Biopharm Ltd. | Methods for treating pancreatic cancer using combination therapies comprising liposomal irinotecan |
| US9717724B2 (en) | 2012-06-13 | 2017-08-01 | Ipsen Biopharm Ltd. | Methods for treating pancreatic cancer using combination therapies |
| US11318131B2 (en) | 2015-05-18 | 2022-05-03 | Ipsen Biopharm Ltd. | Nanoliposomal irinotecan for use in treating small cell lung cancer |
| RU2760185C2 (en) | 2015-08-20 | 2021-11-22 | Ипсен Биофарм Лтд. | Combination therapy using liposomal irinotecan and parp inhibitor for the treatment of cancer |
| WO2017034957A1 (en) | 2015-08-21 | 2017-03-02 | Merrimack Pharmaceuticals, Inc. | Methods for treating metastatic pancreatic cancer using combination therapies comprising liposomal irinotecan and oxaliplatin |
| SG10201912338RA (en) | 2016-11-02 | 2020-02-27 | Ipsen Biopharm Ltd | Treating gastric cancer using combination therapies comprising liposomal irinotecan, oxaliplatin, 5-fluoruracil (and leucovorin) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5227400A (en) * | 1991-09-23 | 1993-07-13 | Florida State University | Furyl and thienyl substituted taxanes and pharmaceutical compositions containing them |
| US5489601A (en) * | 1991-09-23 | 1996-02-06 | Florida State University | Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them |
| EP0690712B1 (en) * | 1993-03-22 | 2001-11-28 | Florida State University | Taxanes having a pyridyl substituted side-chain |
| US5415869A (en) * | 1993-11-12 | 1995-05-16 | The Research Foundation Of State University Of New York | Taxol formulation |
| FR2715307B1 (en) * | 1994-01-25 | 1996-04-05 | Commissariat Energie Atomique | Method for solubilization in an aqueous medium of antitumor agents of the taxol family, and branched cyclodextrins usable for this solubilization. |
| MX9700026A (en) * | 1994-06-28 | 1997-04-30 | Upjohn Co | 7-ether-taxol analogs, antineoplastic use and pharmaceutical compositions containing them. |
-
1996
- 1996-01-31 DE DE19605024A patent/DE19605024A1/en not_active Withdrawn
-
1997
- 1997-01-31 CA CA002244746A patent/CA2244746A1/en not_active Abandoned
- 1997-01-31 CZ CZ19982426A patent/CZ292504B6/en not_active IP Right Cessation
- 1997-01-31 ES ES97902286T patent/ES2192261T3/en not_active Expired - Lifetime
- 1997-01-31 TW TW086101169A patent/TW444015B/en active
- 1997-01-31 KR KR1019980705874A patent/KR19990082151A/en not_active Application Discontinuation
- 1997-01-31 HU HU9901027A patent/HUP9901027A3/en unknown
- 1997-01-31 US US09/117,506 patent/US6162920A/en not_active Expired - Fee Related
- 1997-01-31 CN CN97192006A patent/CN1073108C/en not_active Expired - Fee Related
- 1997-01-31 PT PT97902286T patent/PT896577E/en unknown
- 1997-01-31 EP EP97902286A patent/EP0896577B1/en not_active Expired - Lifetime
- 1997-01-31 ZA ZA9700847A patent/ZA97847B/en unknown
- 1997-01-31 IL IL12495197A patent/IL124951A/en not_active IP Right Cessation
- 1997-01-31 AT AT97902286T patent/ATE233757T1/en not_active IP Right Cessation
- 1997-01-31 RU RU98116122/04A patent/RU2163599C2/en not_active IP Right Cessation
- 1997-01-31 DK DK97902286T patent/DK0896577T3/en active
- 1997-01-31 AU AU15984/97A patent/AU714313B2/en not_active Ceased
- 1997-01-31 SK SK1011-98A patent/SK101198A3/en unknown
- 1997-01-31 PL PL97328055A patent/PL186796B1/en not_active IP Right Cessation
- 1997-01-31 DE DE69719502T patent/DE69719502T2/en not_active Expired - Lifetime
- 1997-01-31 BR BR9708295A patent/BR9708295A/en not_active Application Discontinuation
- 1997-01-31 UA UA98084638A patent/UA49007C2/en unknown
- 1997-01-31 TR TR1998/01415T patent/TR199801415T2/en unknown
- 1997-01-31 WO PCT/EP1997/000440 patent/WO1997028156A1/en not_active Application Discontinuation
- 1997-01-31 JP JP52730897A patent/JP2001505527A/en active Pending
-
1998
- 1998-07-30 NO NO983509A patent/NO983509D0/en unknown
-
1999
- 1999-09-02 HK HK99103795A patent/HK1018778A1/en not_active IP Right Cessation
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9782349B2 (en) | 2004-05-03 | 2017-10-10 | Ipsen Biopharma Ltd. | Liposomes useful for drug delivery |
| US8703181B2 (en) | 2004-05-03 | 2014-04-22 | Merrimack Pharmaceuticals, Inc. | Liposomes useful for drug delivery |
| US8992970B2 (en) | 2004-05-03 | 2015-03-31 | Merrimack Pharmaceuticals, Inc. | Liposomes useful for drug delivery |
| US9717723B2 (en) | 2004-05-03 | 2017-08-01 | Ipsen Biopharm Ltd. | Liposomes useful for drug delivery |
| US9724303B2 (en) | 2004-05-03 | 2017-08-08 | Ipsen Biopharm Ltd. | Liposomes useful for drug delivery |
| US9730891B2 (en) | 2004-05-03 | 2017-08-15 | Ipsen Biopharm Ltd. | Liposomes useful for drug delivery |
| US8658203B2 (en) | 2004-05-03 | 2014-02-25 | Merrimack Pharmaceuticals, Inc. | Liposomes useful for drug delivery to the brain |
| US10350201B2 (en) | 2004-05-03 | 2019-07-16 | Ipsen Biopharm Ltd. | Liposomes useful for drug delivery |
| US10722508B2 (en) | 2004-05-03 | 2020-07-28 | Ipsen Biopharm Ltd. | Liposomes useful for drug delivery |
| US11052079B2 (en) | 2004-05-03 | 2021-07-06 | Ipsen Biopharm Ltd. | Liposomes useful for drug delivery |
| RU2757110C2 (en) * | 2004-05-03 | 2021-10-11 | Ипсен Биофарм Лтд. | Liposomal compositions used for drug delivery |
| US10456360B2 (en) | 2015-10-16 | 2019-10-29 | Ipsen Biopharm Ltd. | Stabilizing camptothecin pharmaceutical compositions |
| US10993914B2 (en) | 2015-10-16 | 2021-05-04 | Ipsen Biopharm Ltd. | Stabilizing camptothecin pharmaceutical compositions |
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