NZ563054A - Antitumoral tetrahydro-pyrimidines - Google Patents
Antitumoral tetrahydro-pyrimidinesInfo
- Publication number
- NZ563054A NZ563054A NZ563054A NZ56305406A NZ563054A NZ 563054 A NZ563054 A NZ 563054A NZ 563054 A NZ563054 A NZ 563054A NZ 56305406 A NZ56305406 A NZ 56305406A NZ 563054 A NZ563054 A NZ 563054A
- Authority
- NZ
- New Zealand
- Prior art keywords
- substituted
- unsubstituted
- optionally substituted
- alkyl
- compound
- Prior art date
Links
- 230000000259 anti-tumor effect Effects 0.000 title description 7
- 150000005326 tetrahydropyrimidines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 239000000651 prodrug Substances 0.000 claims abstract description 16
- 229940002612 prodrug Drugs 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 14
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
- 201000011510 cancer Diseases 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 241000498224 Meandrina meandrites Species 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- -1 alkenynyl Chemical group 0.000 claims description 17
- 229940126062 Compound A Drugs 0.000 claims description 16
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- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 5
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- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 5
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
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- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
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- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 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
- 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
- 238000002000 high resolution fast-atom bombardment mass spectrometry Methods 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical group C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 125000001041 indolyl group Chemical group 0.000 description 1
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- 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
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
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- 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
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- 229940049954 penicillin Drugs 0.000 description 1
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- 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000007747 plating Methods 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 238000007614 solvation Methods 0.000 description 1
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- 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
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- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
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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 (1)
| Publication Number | Publication Date |
|---|---|
| NZ563054A true NZ563054A (en) | 2010-09-30 |
Family
ID=36649783
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ563054A NZ563054A (en) | 2005-05-03 | 2006-05-03 | Antitumoral tetrahydro-pyrimidines |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20100216817A1 (https=) |
| EP (1) | EP1879870A1 (https=) |
| JP (1) | JP2008540362A (https=) |
| KR (1) | KR20080007640A (https=) |
| CN (1) | CN101171236A (https=) |
| AU (1) | AU2006243407A1 (https=) |
| CA (1) | CA2605784A1 (https=) |
| EA (1) | EA013160B1 (https=) |
| IL (1) | IL186781A0 (https=) |
| MX (1) | MX2007013683A (https=) |
| NO (1) | NO20076162L (https=) |
| NZ (1) | NZ563054A (https=) |
| WO (1) | WO2006117197A1 (https=) |
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 |
| HRP20231233T1 (hr) | 2017-04-27 | 2024-01-19 | Pharma Mar, S.A. | Antitumorski spojevi |
| 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 |
Family Cites Families (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 CN CNA2006800149611A patent/CN101171236A/zh active Pending
- 2006-05-03 KR KR1020077027731A patent/KR20080007640A/ko not_active Withdrawn
- 2006-05-03 CA CA002605784A patent/CA2605784A1/en not_active Abandoned
- 2006-05-03 EP EP06742776A patent/EP1879870A1/en not_active Withdrawn
- 2006-05-03 MX MX2007013683A patent/MX2007013683A/es not_active Application Discontinuation
- 2006-05-03 NZ NZ563054A patent/NZ563054A/en unknown
- 2006-05-03 US US11/913,513 patent/US20100216817A1/en not_active Abandoned
- 2006-05-03 JP JP2008509372A patent/JP2008540362A/ja not_active Withdrawn
- 2006-05-03 EA EA200702397A patent/EA013160B1/ru not_active IP Right Cessation
- 2006-05-03 AU AU2006243407A patent/AU2006243407A1/en not_active Abandoned
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007013683A (es) | 2007-12-03 |
| EA013160B1 (ru) | 2010-02-26 |
| CA2605784A1 (en) | 2006-11-09 |
| EP1879870A1 (en) | 2008-01-23 |
| US20100216817A1 (en) | 2010-08-26 |
| IL186781A0 (en) | 2008-02-09 |
| NO20076162L (no) | 2007-11-29 |
| JP2008540362A (ja) | 2008-11-20 |
| WO2006117197A1 (en) | 2006-11-09 |
| CN101171236A (zh) | 2008-04-30 |
| AU2006243407A1 (en) | 2006-11-09 |
| EA200702397A1 (ru) | 2008-02-28 |
| KR20080007640A (ko) | 2008-01-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed |