EA013160B1 - Противоопухолевые тетрагидропиримидины - Google Patents
Противоопухолевые тетрагидропиримидины Download PDFInfo
- Publication number
- EA013160B1 EA013160B1 EA200702397A EA200702397A EA013160B1 EA 013160 B1 EA013160 B1 EA 013160B1 EA 200702397 A EA200702397 A EA 200702397A EA 200702397 A EA200702397 A EA 200702397A EA 013160 B1 EA013160 B1 EA 013160B1
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- EA
- Eurasian Patent Office
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- compound according
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- SKKTUOZKZKCGTB-UHFFFAOYSA-N butyl carbamate Chemical compound CCCCOC(N)=O SKKTUOZKZKCGTB-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000036755 cellular response Effects 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 201000010288 cervix melanoma Diseases 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- 201000010897 colon adenocarcinoma Diseases 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000002716 delivery method Methods 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000011978 dissolution method Methods 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- SLXGSHUENGHGJZ-UHFFFAOYSA-N formyl octanoate Chemical compound CCCCCCCC(=O)OC=O SLXGSHUENGHGJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 239000012520 frozen sample Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 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 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical compound IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 description 1
- NAVMMSRRNOXQMJ-UHFFFAOYSA-M iodomethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CI)C1=CC=CC=C1 NAVMMSRRNOXQMJ-UHFFFAOYSA-M 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XFKBFTDXRXAOFV-UHFFFAOYSA-N methyl 10-iododec-9-enoate Chemical compound COC(=O)CCCCCCCC=CI XFKBFTDXRXAOFV-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
- 239000002077 nanosphere Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- UUSZLLQJYRSZIS-LXNNNBEUSA-N plitidepsin Chemical compound CN([C@H](CC(C)C)C(=O)N[C@@H]1C(=O)N[C@@H]([C@H](CC(=O)O[C@H](C(=O)[C@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(OC)=CC=2)C(=O)O[C@@H]1C)C(C)C)O)[C@@H](C)CC)C(=O)[C@@H]1CCCN1C(=O)C(C)=O UUSZLLQJYRSZIS-LXNNNBEUSA-N 0.000 description 1
- 229950008499 plitidepsin Drugs 0.000 description 1
- 108010049948 plitidepsin Proteins 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- JBDKAABFESSFMV-UHFFFAOYSA-N pyrrolo[1,2-a]pyrimidine Chemical class N1=CC=CN2C=CC=C21 JBDKAABFESSFMV-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05076037 | 2005-05-03 | ||
| PCT/EP2006/004117 WO2006117197A1 (en) | 2005-05-03 | 2006-05-03 | Antitumoral tetrahydro-pyrimidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200702397A1 EA200702397A1 (ru) | 2008-02-28 |
| EA013160B1 true EA013160B1 (ru) | 2010-02-26 |
Family
ID=36649783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200702397A EA013160B1 (ru) | 2005-05-03 | 2006-05-03 | Противоопухолевые тетрагидропиримидины |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20100216817A1 (enExample) |
| EP (1) | EP1879870A1 (enExample) |
| JP (1) | JP2008540362A (enExample) |
| KR (1) | KR20080007640A (enExample) |
| CN (1) | CN101171236A (enExample) |
| AU (1) | AU2006243407A1 (enExample) |
| CA (1) | CA2605784A1 (enExample) |
| EA (1) | EA013160B1 (enExample) |
| IL (1) | IL186781A0 (enExample) |
| MX (1) | MX2007013683A (enExample) |
| NO (1) | NO20076162L (enExample) |
| NZ (1) | NZ563054A (enExample) |
| WO (1) | WO2006117197A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102210868A (zh) * | 2011-04-29 | 2011-10-12 | 济南环肽医药科技有限公司 | 四氢嘧啶及其衍生物在制备口服吸收促进剂中的应用 |
| LT3615544T (lt) | 2017-04-27 | 2023-05-10 | Pharma Mar S.A. | Priešnavikiniai junginiai |
| CN108120792B (zh) * | 2017-12-14 | 2020-03-24 | 青海出入境检验检疫局检验检疫综合技术中心 | 一种四氢嘧啶的高效液相检测及含量测定方法 |
| CN110156697B (zh) * | 2019-05-30 | 2022-05-06 | 常州沃腾化工科技有限公司 | 一种1,2-二甲基-1,4,5,6-四氢嘧啶的合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2743255A (en) * | 1952-12-19 | 1956-04-24 | Petrolite Corp | Amine-modified thermoplastic phenolaldehyde resins and method of making same |
| US4292429A (en) * | 1978-03-08 | 1981-09-29 | Ciba-Geigy Corporation | Imidazole urea and amido compounds |
-
2006
- 2006-05-03 KR KR1020077027731A patent/KR20080007640A/ko not_active Withdrawn
- 2006-05-03 CN CNA2006800149611A patent/CN101171236A/zh active Pending
- 2006-05-03 MX MX2007013683A patent/MX2007013683A/es not_active Application Discontinuation
- 2006-05-03 US US11/913,513 patent/US20100216817A1/en not_active Abandoned
- 2006-05-03 EA EA200702397A patent/EA013160B1/ru not_active IP Right Cessation
- 2006-05-03 JP JP2008509372A patent/JP2008540362A/ja not_active Withdrawn
- 2006-05-03 CA CA002605784A patent/CA2605784A1/en not_active Abandoned
- 2006-05-03 AU AU2006243407A patent/AU2006243407A1/en not_active Abandoned
- 2006-05-03 NZ NZ563054A patent/NZ563054A/en unknown
- 2006-05-03 EP EP06742776A patent/EP1879870A1/en not_active Withdrawn
- 2006-05-03 WO PCT/EP2006/004117 patent/WO2006117197A1/en not_active Ceased
-
2007
- 2007-10-18 IL IL186781A patent/IL186781A0/en unknown
- 2007-11-29 NO NO20076162A patent/NO20076162L/no not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2743255A (en) * | 1952-12-19 | 1956-04-24 | Petrolite Corp | Amine-modified thermoplastic phenolaldehyde resins and method of making same |
| US4292429A (en) * | 1978-03-08 | 1981-09-29 | Ciba-Geigy Corporation | Imidazole urea and amido compounds |
Non-Patent Citations (1)
| Title |
|---|
| KOURANY-LEFOLL E. ET AL.: "Phloeodictines A1-A7 and C1-C2, antibiotic and cytotoxic guanidine alkaloids from the New Caledonian sponge phloeodictyon sp.". TETRAHEDRON, vol. 50, no. 11, 14 March, 1994 (1994-03-14), pages 3415-3426, XP002391145, cited in the application, the whole document * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008540362A (ja) | 2008-11-20 |
| KR20080007640A (ko) | 2008-01-22 |
| NZ563054A (en) | 2010-09-30 |
| EP1879870A1 (en) | 2008-01-23 |
| CN101171236A (zh) | 2008-04-30 |
| MX2007013683A (es) | 2007-12-03 |
| NO20076162L (no) | 2007-11-29 |
| AU2006243407A1 (en) | 2006-11-09 |
| CA2605784A1 (en) | 2006-11-09 |
| US20100216817A1 (en) | 2010-08-26 |
| IL186781A0 (en) | 2008-02-09 |
| WO2006117197A1 (en) | 2006-11-09 |
| EA200702397A1 (ru) | 2008-02-28 |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): RU |