JP2003532677A - ペプチドデホルミラーゼ阻害物質 - Google Patents
ペプチドデホルミラーゼ阻害物質Info
- Publication number
- JP2003532677A JP2003532677A JP2001581824A JP2001581824A JP2003532677A JP 2003532677 A JP2003532677 A JP 2003532677A JP 2001581824 A JP2001581824 A JP 2001581824A JP 2001581824 A JP2001581824 A JP 2001581824A JP 2003532677 A JP2003532677 A JP 2003532677A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- formyl
- ethylamine
- group
- optionally substituted
- 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.)
- Pending
Links
- 239000000081 peptide deformylase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 36
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 26
- -1 hydroxy, amino Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- VZYOJQGXIVZHJA-UHFFFAOYSA-N n-hydroxy-n-(2-isoquinolin-5-yloxyethyl)formamide Chemical compound N1=CC=C2C(OCCN(O)C=O)=CC=CC2=C1 VZYOJQGXIVZHJA-UHFFFAOYSA-N 0.000 claims description 4
- PKIJUBJUZCGQFK-UHFFFAOYSA-N n-hydroxy-n-(4-phenylbutyl)formamide Chemical compound O=CN(O)CCCCC1=CC=CC=C1 PKIJUBJUZCGQFK-UHFFFAOYSA-N 0.000 claims description 4
- SRSKXJVMVSSSHB-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine Chemical compound N1=CC=C2NC=CC2=C1 SRSKXJVMVSSSHB-UHFFFAOYSA-N 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- QMMXVSWFTWAHHR-UHFFFAOYSA-N n-[2-(2,3-dichlorophenoxy)ethyl]-n-hydroxyformamide Chemical compound O=CN(O)CCOC1=CC=CC(Cl)=C1Cl QMMXVSWFTWAHHR-UHFFFAOYSA-N 0.000 claims description 3
- YTZZQFYDELXOBH-UHFFFAOYSA-N n-[2-(3,5-dichlorophenoxy)ethyl]-n-hydroxyformamide Chemical compound O=CN(O)CCOC1=CC(Cl)=CC(Cl)=C1 YTZZQFYDELXOBH-UHFFFAOYSA-N 0.000 claims description 3
- RRVPFFRQJWCUHT-UHFFFAOYSA-N n-[2-(3-bromophenoxy)ethyl]-n-hydroxyformamide Chemical compound O=CN(O)CCOC1=CC=CC(Br)=C1 RRVPFFRQJWCUHT-UHFFFAOYSA-N 0.000 claims description 3
- CAWOEYFABGWIIU-UHFFFAOYSA-N n-[2-(4-acetylphenoxy)ethyl]-n-hydroxyformamide Chemical compound CC(=O)C1=CC=C(OCCN(O)C=O)C=C1 CAWOEYFABGWIIU-UHFFFAOYSA-N 0.000 claims description 3
- FWMFAPOFUVHBBR-UHFFFAOYSA-N n-[2-(4-chloro-3-methylphenoxy)ethyl]-n-hydroxyformamide Chemical compound CC1=CC(OCCN(O)C=O)=CC=C1Cl FWMFAPOFUVHBBR-UHFFFAOYSA-N 0.000 claims description 3
- WGSZRNPBPRGDGP-UHFFFAOYSA-N n-hydroxy-n-(2-naphthalen-2-yloxyethyl)formamide Chemical compound C1=CC=CC2=CC(OCCN(O)C=O)=CC=C21 WGSZRNPBPRGDGP-UHFFFAOYSA-N 0.000 claims description 3
- ZKSWGBQVZSYTRA-UHFFFAOYSA-N n-hydroxy-n-(2-quinolin-7-yloxyethyl)formamide Chemical compound C1=CC=NC2=CC(OCCN(O)C=O)=CC=C21 ZKSWGBQVZSYTRA-UHFFFAOYSA-N 0.000 claims description 3
- QPOHGXYNCHVSMF-UHFFFAOYSA-N n-hydroxy-n-(3-phenylpropyl)formamide Chemical compound O=CN(O)CCCC1=CC=CC=C1 QPOHGXYNCHVSMF-UHFFFAOYSA-N 0.000 claims description 3
- XVTICJBXUDISEU-UHFFFAOYSA-N n-hydroxy-n-[2-[2-(trifluoromethyl)phenoxy]ethyl]formamide Chemical compound O=CN(O)CCOC1=CC=CC=C1C(F)(F)F XVTICJBXUDISEU-UHFFFAOYSA-N 0.000 claims description 3
- PCENRYQAUFQBJN-UHFFFAOYSA-N n-hydroxy-n-[3-(3-methylpyridin-2-yl)propyl]formamide Chemical compound CC1=CC=CN=C1CCCN(O)C=O PCENRYQAUFQBJN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- STDNJYNAFFNJSP-UHFFFAOYSA-N n-[2-(2-chlorophenoxy)ethyl]-n-hydroxyformamide Chemical compound O=CN(O)CCOC1=CC=CC=C1Cl STDNJYNAFFNJSP-UHFFFAOYSA-N 0.000 claims description 2
- VSDQSNOWVKGAOS-UHFFFAOYSA-N n-[2-(3-chloro-4-methylphenoxy)ethyl]-n-hydroxyformamide Chemical compound CC1=CC=C(OCCN(O)C=O)C=C1Cl VSDQSNOWVKGAOS-UHFFFAOYSA-N 0.000 claims description 2
- TZVMAWSTSVCZMT-UHFFFAOYSA-N n-hydroxy-n-(2-naphthalen-1-yloxyethyl)formamide Chemical compound C1=CC=C2C(OCCN(O)C=O)=CC=CC2=C1 TZVMAWSTSVCZMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- OLPYCUUQHBSPJW-UHFFFAOYSA-N 3-phenyl-1h-pyrrolo[3,2-c]pyridine Chemical group C=1NC2=CC=NC=C2C=1C1=CC=CC=C1 OLPYCUUQHBSPJW-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 241000194033 Enterococcus Species 0.000 claims 1
- 241000191940 Staphylococcus Species 0.000 claims 1
- 241000194017 Streptococcus Species 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000012230 colorless oil Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- KDGKTJGPFXIBEB-UHFFFAOYSA-N n-hydroxyformamide Chemical compound ONC=O KDGKTJGPFXIBEB-UHFFFAOYSA-N 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000002923 oximes Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 5
- 241000588724 Escherichia coli Species 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 4
- 101710181812 Methionine aminopeptidase Proteins 0.000 description 4
- 108010026809 Peptide deformylase Proteins 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
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- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
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- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 238000004007 reversed phase HPLC Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 102100021418 Peptide deformylase, mitochondrial Human genes 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 3
- 230000014616 translation Effects 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/14—Hydroxylamino compounds or their ethers or esters having nitrogen atoms of hydroxylamino groups further bound to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20194300P | 2000-05-05 | 2000-05-05 | |
| US60/201,943 | 2000-05-05 | ||
| US23808400P | 2000-10-04 | 2000-10-04 | |
| US60/238,084 | 2000-10-04 | ||
| PCT/US2001/014593 WO2001085170A1 (en) | 2000-05-05 | 2001-05-04 | Peptide deformylase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003532677A true JP2003532677A (ja) | 2003-11-05 |
| JP2003532677A5 JP2003532677A5 (enExample) | 2008-06-19 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2001581824A Pending JP2003532677A (ja) | 2000-05-05 | 2001-05-04 | ペプチドデホルミラーゼ阻害物質 |
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| Country | Link |
|---|---|
| US (2) | US6806369B2 (enExample) |
| EP (1) | EP1283711B1 (enExample) |
| JP (1) | JP2003532677A (enExample) |
| KR (1) | KR20020093127A (enExample) |
| CN (1) | CN1427721A (enExample) |
| AR (1) | AR029916A1 (enExample) |
| AT (1) | ATE389403T1 (enExample) |
| AU (1) | AU2001261218A1 (enExample) |
| BR (1) | BR0110206A (enExample) |
| CA (1) | CA2408236A1 (enExample) |
| CZ (1) | CZ20023618A3 (enExample) |
| DE (1) | DE60133273T2 (enExample) |
| ES (1) | ES2300330T3 (enExample) |
| HU (1) | HUP0302505A2 (enExample) |
| IL (1) | IL152638A0 (enExample) |
| MX (1) | MXPA02010843A (enExample) |
| NO (1) | NO20025281L (enExample) |
| NZ (1) | NZ521560A (enExample) |
| PL (1) | PL359865A1 (enExample) |
| WO (1) | WO2001085170A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008528455A (ja) * | 2005-01-21 | 2008-07-31 | サントル ナシオナル ドゥ ラ ルシェルシェ シアンティフィク | ペプチドデホルミラーゼ阻害物質、その使用、及びそれを含む医薬組成物 |
| JP2008545765A (ja) * | 2005-06-07 | 2008-12-18 | ノバルティス アクチエンゲゼルシャフト | ペプチドデホルミラーゼ（ｐｄｆ）阻害剤４ |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1383736B1 (en) * | 2001-04-05 | 2009-06-17 | Smithkline Beecham Corporation | Peptide deformylase inhibitors |
| AU2002322035A1 (en) * | 2001-06-05 | 2002-12-16 | Smithkline Beecham Corporation | Peptide deformylase inhibitors |
| WO2004052919A2 (en) * | 2002-12-11 | 2004-06-24 | Smithkline Beecham Corporation | Peptide deformylase inhibitors |
| EP1877407A1 (en) * | 2005-04-25 | 2008-01-16 | Novartis AG | Imidazo(1,2-a)pyridine derivatives useful as peptide deformylase (pdf) inhibitors |
| DE102005019181A1 (de) * | 2005-04-25 | 2006-10-26 | Novartis Ag | Peptid-Deformylase (PDF) Inhibitoren 1 |
| WO2007040289A1 (en) * | 2005-10-05 | 2007-04-12 | Promeditech Inc. | Deformylase inhibitor, process for the preparation thereof, and composition comprising the same |
| KR100753796B1 (ko) * | 2006-07-28 | 2007-08-31 | 주식회사 프로메디텍 | 데포르밀라제 저해제, 이의 제조방법, 및 이를 포함하는조성물 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987004152A1 (en) * | 1985-12-30 | 1987-07-16 | The Wellcome Foundation Ltd. | New aryl derivatives |
| WO1999039704A1 (en) * | 1998-02-07 | 1999-08-12 | British Biotech Pharmaceuticals Limited | Antibacterial agents |
| JP2003532673A (ja) * | 2000-05-05 | 2003-11-05 | スミスクライン・ビーチャム・コーポレイション | ペプチドデホルミラーゼ阻害物質 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3282986A (en) | 1960-10-06 | 1966-11-01 | Merck & Co Inc | N-acylated hydroxamic acids and derivatives thereof |
| IL78157A (en) | 1985-03-16 | 1989-08-15 | Wellcome Found | Aryl derivatives,their preparation and pharmaceutical compositions containing them |
| PL154186B1 (en) * | 1987-07-15 | 1991-07-31 | Wellcome Found | Method for manufacturing arylic derivatives of the hydroxamic acid |
| HUP0002037A3 (en) | 1997-07-31 | 2001-07-30 | Abbott Lab | Hydroximic acid derivatives, use of them for producing pharmaceutical compositions suitable for inhibiting matrix metalloproteinas and pharmaceutical compositions containing the compounds |
| US6235786B1 (en) * | 1997-08-06 | 2001-05-22 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| US6294573B1 (en) * | 1997-08-06 | 2001-09-25 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| US20040034024A1 (en) | 2001-05-04 | 2004-02-19 | Aubart Kelly M | Peptide deformylase inhibitors |
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2001
- 2001-05-03 AR ARP010102092A patent/AR029916A1/es not_active Application Discontinuation
- 2001-05-04 CN CN01808997A patent/CN1427721A/zh active Pending
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- 2001-05-04 IL IL15263801A patent/IL152638A0/xx unknown
- 2001-05-04 JP JP2001581824A patent/JP2003532677A/ja active Pending
- 2001-05-04 KR KR1020027014802A patent/KR20020093127A/ko not_active Withdrawn
- 2001-05-04 AU AU2001261218A patent/AU2001261218A1/en not_active Abandoned
- 2001-05-04 HU HU0302505A patent/HUP0302505A2/hu unknown
- 2001-05-04 DE DE60133273T patent/DE60133273T2/de not_active Expired - Lifetime
- 2001-05-04 MX MXPA02010843A patent/MXPA02010843A/es unknown
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- 2001-05-04 PL PL35986501A patent/PL359865A1/xx unknown
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- 2001-05-04 US US10/275,522 patent/US6806369B2/en not_active Expired - Fee Related
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- 2001-05-04 CA CA002408236A patent/CA2408236A1/en not_active Abandoned
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2002
- 2002-11-04 NO NO20025281A patent/NO20025281L/no not_active Application Discontinuation
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2004
- 2004-04-05 US US10/818,074 patent/US7115605B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987004152A1 (en) * | 1985-12-30 | 1987-07-16 | The Wellcome Foundation Ltd. | New aryl derivatives |
| WO1999039704A1 (en) * | 1998-02-07 | 1999-08-12 | British Biotech Pharmaceuticals Limited | Antibacterial agents |
| JP2003532673A (ja) * | 2000-05-05 | 2003-11-05 | スミスクライン・ビーチャム・コーポレイション | ペプチドデホルミラーゼ阻害物質 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008528455A (ja) * | 2005-01-21 | 2008-07-31 | サントル ナシオナル ドゥ ラ ルシェルシェ シアンティフィク | ペプチドデホルミラーゼ阻害物質、その使用、及びそれを含む医薬組成物 |
| JP2008545765A (ja) * | 2005-06-07 | 2008-12-18 | ノバルティス アクチエンゲゼルシャフト | ペプチドデホルミラーゼ（ｐｄｆ）阻害剤４ |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001085170A9 (en) | 2006-01-26 |
| MXPA02010843A (es) | 2003-03-27 |
| CZ20023618A3 (cs) | 2003-09-17 |
| EP1283711A1 (en) | 2003-02-19 |
| US20040053932A1 (en) | 2004-03-18 |
| PL359865A1 (en) | 2004-09-06 |
| EP1283711B1 (en) | 2008-03-19 |
| NO20025281L (no) | 2003-01-03 |
| CA2408236A1 (en) | 2001-11-15 |
| ATE389403T1 (de) | 2008-04-15 |
| CN1427721A (zh) | 2003-07-02 |
| US7115605B2 (en) | 2006-10-03 |
| HUP0302505A2 (hu) | 2003-12-29 |
| ES2300330T3 (es) | 2008-06-16 |
| AR029916A1 (es) | 2003-07-23 |
| AU2001261218A1 (en) | 2001-11-20 |
| NZ521560A (en) | 2004-05-28 |
| BR0110206A (pt) | 2003-01-28 |
| NO20025281D0 (no) | 2002-11-04 |
| US6806369B2 (en) | 2004-10-19 |
| EP1283711A4 (en) | 2003-05-21 |
| IL152638A0 (en) | 2003-06-24 |
| KR20020093127A (ko) | 2002-12-12 |
| WO2001085170A1 (en) | 2001-11-15 |
| DE60133273T2 (de) | 2009-03-05 |
| DE60133273D1 (de) | 2008-04-30 |
| US20040192719A1 (en) | 2004-09-30 |
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