JP2011529921A5 - - Google Patents
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- Publication number
- JP2011529921A5 JP2011529921A5 JP2011521364A JP2011521364A JP2011529921A5 JP 2011529921 A5 JP2011529921 A5 JP 2011529921A5 JP 2011521364 A JP2011521364 A JP 2011521364A JP 2011521364 A JP2011521364 A JP 2011521364A JP 2011529921 A5 JP2011529921 A5 JP 2011529921A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- item
- cycloalkyl
- compound
- heterocycloalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 114
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 27
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 27
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 27
- 150000001413 amino acids Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- -1 R 21 Chemical compound 0.000 claims description 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000004471 Glycine Substances 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 8
- 208000015181 infectious disease Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 244000005700 microbiome Species 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 5
- 241000233866 Fungi Species 0.000 claims description 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical group C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 5
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical group CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 5
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical group CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 5
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical group CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 5
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Chemical group CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 5
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Chemical group CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 5
- 235000004279 alanine Nutrition 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000001475 halogen functional group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229960000310 isoleucine Drugs 0.000 claims description 5
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Chemical group CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000004001 thioalkyl group Chemical group 0.000 claims description 5
- 150000003573 thiols Chemical class 0.000 claims description 5
- 239000004474 valine Chemical group 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- YELDUWMYYRJMJD-UHFFFAOYSA-N 2-sulfamoylguanidine Chemical compound NC(N)=NS(N)(=O)=O YELDUWMYYRJMJD-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000001243 protein synthesis Methods 0.000 claims description 2
- 230000014616 translation Effects 0.000 claims description 2
- 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 101150024084 nhr-28 gene Proteins 0.000 claims 1
- 238000000034 method Methods 0.000 description 82
- 229940024606 amino acid Drugs 0.000 description 15
- 235000001014 amino acid Nutrition 0.000 description 15
- 125000000547 substituted alkyl group Chemical group 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 241000700605 Viruses Species 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- CEUKVIUTWQHCJM-UHFFFAOYSA-N CSCCC(CS(O)(=O)=O)NC(CN)=O Chemical compound CSCCC(CS(O)(=O)=O)NC(CN)=O CEUKVIUTWQHCJM-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8555608P | 2008-08-01 | 2008-08-01 | |
| US61/085,556 | 2008-08-01 | ||
| PCT/US2009/052474 WO2010014943A2 (en) | 2008-08-01 | 2009-07-31 | Methionine analogs and methods of using same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011529921A JP2011529921A (ja) | 2011-12-15 |
| JP2011529921A5 true JP2011529921A5 (https=) | 2012-09-13 |
| JP5650642B2 JP5650642B2 (ja) | 2015-01-07 |
Family
ID=41414372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011521364A Expired - Fee Related JP5650642B2 (ja) | 2008-08-01 | 2009-07-31 | メチオニンアナログおよびそれらを使用する方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (5) | US8580859B2 (https=) |
| EP (1) | EP2326619B1 (https=) |
| JP (1) | JP5650642B2 (https=) |
| CN (1) | CN102171185A (https=) |
| AU (1) | AU2009276343A1 (https=) |
| CA (1) | CA2733390A1 (https=) |
| IL (1) | IL210956A0 (https=) |
| WO (1) | WO2010014943A2 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102171185A (zh) | 2008-08-01 | 2011-08-31 | 拜奥西尼斯医药股份有限公司 | 甲硫氨酸类似物及其使用方法 |
| US9200251B1 (en) | 2011-03-31 | 2015-12-01 | David Gordon Bermudes | Bacterial methionine analogue and methionine synthesis inhibitor anticancer, antiinfective and coronary heart disease protective microcins and methods of treatment therewith |
| WO2019169029A1 (en) | 2018-02-28 | 2019-09-06 | Bioxiness Pharmaceuticals, Inc. | Target specific chemotherapeutic agents |
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| FR961832A (https=) | 1943-03-20 | 1950-05-23 | ||
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| FR1390191A (fr) | 1963-07-19 | 1965-02-26 | Dehydag Gmbh | Procédé de préparation de sulfobétaïnes à bases hétérocycliques de type aromatique |
| US3519683A (en) | 1967-03-31 | 1970-07-07 | Meiji Seika Co | Process for preparing 5-amino-5-deoxy-d-glucose-1-sulfonic acid |
| GB1580899A (en) | 1976-07-27 | 1980-12-10 | Fujisawa Pharmaceutical Co | Hydroxyaminohydrocarbonphosphonic acid derivatives and production and use thereof |
| JPS5463024A (en) | 1977-10-27 | 1979-05-21 | Fujisawa Pharmaceut Co Ltd | 3-(n-formyl-n-hydroxyamino)-2(r)-hydroxypropyl-phosphonic acid, its preparation, and its use |
| US4169950A (en) | 1977-12-08 | 1979-10-02 | Research Organics | Amino-hydroxy-alkyl sulfonic acid zwitterions |
| IL61985A0 (en) | 1980-02-01 | 1981-02-27 | Sparamedica Ag | Phosphinic and phosphonic acid derivatives,their manufacture and pharmaceutical compositions containing them |
| DE3273586D1 (en) | 1981-11-02 | 1986-11-06 | Ici Plc | Substituted propyl phosphonic acid derivatives, their use as herbicides, herbicidal compositions containing them, and methods of preparing them |
| DE3245887A1 (de) | 1982-12-11 | 1984-06-14 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung substituierter phosphon und phosphinsaeuren |
| GB8308506D0 (en) | 1983-03-28 | 1983-05-05 | Ici Plc | Heterocyclic compounds |
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| DE3435156A1 (de) | 1984-09-25 | 1986-04-03 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zur herstellung der stereoisomeren von 1-amino-alkylphosphonsaeuren oder 1-aminoalkylphosphinsaeuren |
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| IT1211792B (it) | 1987-09-21 | 1989-11-03 | Sigma Tau Ind Farmaceuti | O-alcanoil derivati dell'acido 3ammino-2-idrossipropansolfonico adattivita'anticonvulsivante e loro composizioni farmaceutiche per il trattamento terapeutico dell'epilessia |
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| DK2839830T3 (da) * | 2005-01-14 | 2019-08-19 | Urigen Inc | Kits og sammensætninger til behandling af lidelser i de nedre urinveje |
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| AU2008333929A1 (en) | 2007-12-03 | 2009-06-11 | Signum Biosciences, Inc. | Acid mimic compounds for the inhibition of isoprenyl-S-cysteinyl methyltransferase |
| CN102171185A (zh) | 2008-08-01 | 2011-08-31 | 拜奥西尼斯医药股份有限公司 | 甲硫氨酸类似物及其使用方法 |
-
2009
- 2009-07-31 CN CN2009801390134A patent/CN102171185A/zh active Pending
- 2009-07-31 CA CA2733390A patent/CA2733390A1/en not_active Abandoned
- 2009-07-31 AU AU2009276343A patent/AU2009276343A1/en not_active Abandoned
- 2009-07-31 JP JP2011521364A patent/JP5650642B2/ja not_active Expired - Fee Related
- 2009-07-31 EP EP09791073.1A patent/EP2326619B1/en not_active Not-in-force
- 2009-07-31 WO PCT/US2009/052474 patent/WO2010014943A2/en not_active Ceased
- 2009-07-31 US US13/056,102 patent/US8580859B2/en not_active Expired - Fee Related
-
2011
- 2011-01-30 IL IL210956A patent/IL210956A0/en unknown
-
2013
- 2013-10-07 US US14/047,845 patent/US20140142189A1/en not_active Abandoned
-
2014
- 2014-12-10 US US14/565,970 patent/US20150329481A1/en not_active Abandoned
-
2016
- 2016-02-26 US US15/054,761 patent/US9695119B2/en not_active Expired - Fee Related
-
2017
- 2017-06-01 US US15/611,575 patent/US20170267632A1/en not_active Abandoned
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