AU2001255391A1 - Halogentated 2-amino-5,6 heptenoic acid derivatives useful as nitric oxide synthase inhibitors - Google Patents

Halogentated 2-amino-5,6 heptenoic acid derivatives useful as nitric oxide synthase inhibitors

Info

Publication number: AU2001255391A1
Authority: AU; Australia
Prior art keywords: amino; halo; group; alkyl; compound
Prior art date: 2000-04-13
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.): Abandoned

Application number

AU2001255391A

Other languages

English (en)

Inventor

Alok K. Awasthi

Margaret L. Grapperhaus

Donald W. Hansen Jr.

Pamela T. Manning

Barnett S Pitzele

James A Sikorski

Lijuan J. Wang

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia LLC

Original Assignee

Pharmacia LLC

Priority date (The priority date 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 date listed.)

2000-04-13

Filing date

2001-04-13

Publication date

2001-10-30

2001-04-13 Application filed by Pharmacia LLC filed Critical Pharmacia LLC

2001-10-30 Publication of AU2001255391A1 publication Critical patent/AU2001255391A1/en

Status Abandoned legal-status Critical Current

Links

239000000236 nitric oxide synthase inhibitor Substances 0.000 title description 6
CSYSULGPHGCBQD-UHFFFAOYSA-N s-ethylisothiouronium diethylphosphate Chemical compound CCSC(N)=N.CCOP(O)(=O)OCC CSYSULGPHGCBQD-UHFFFAOYSA-N 0.000 title description 6
FLYIRERUSAMCDQ-UHFFFAOYSA-N 2-azaniumyl-2-(2-methylphenyl)acetate Chemical class CC1=CC=CC=C1C(N)C(O)=O FLYIRERUSAMCDQ-UHFFFAOYSA-N 0.000 title description 2
-1 heteroaralkoxy Chemical group 0.000 claims description 248
125000005843 halogen group Chemical group 0.000 claims description 215
150000001875 compounds Chemical class 0.000 claims description 192
229910052739 hydrogen Inorganic materials 0.000 claims description 136
125000000217 alkyl group Chemical group 0.000 claims description 118
150000003839 salts Chemical class 0.000 claims description 81
229910052731 fluorine Inorganic materials 0.000 claims description 69
125000000623 heterocyclic group Chemical group 0.000 claims description 66
239000011737 fluorine Substances 0.000 claims description 61
125000001153 fluoro group Chemical group F* 0.000 claims description 52
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 44
238000000034 method Methods 0.000 claims description 39
125000003545 alkoxy group Chemical group 0.000 claims description 34
238000011282 treatment Methods 0.000 claims description 34
125000000304 alkynyl group Chemical group 0.000 claims description 31
125000003710 aryl alkyl group Chemical group 0.000 claims description 30
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
229910052757 nitrogen Inorganic materials 0.000 claims description 25
229910052799 carbon Inorganic materials 0.000 claims description 23
206010028980 Neoplasm Diseases 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 20
229910052717 sulfur Inorganic materials 0.000 claims description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 17
125000004414 alkyl thio group Chemical group 0.000 claims description 17
125000003118 aryl group Chemical group 0.000 claims description 17
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 17
125000001072 heteroaryl group Chemical group 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 16
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 16
125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
125000004438 haloalkoxy group Chemical group 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 16
239000011347 resin Substances 0.000 claims description 16
229920005989 resin Polymers 0.000 claims description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
125000005354 acylalkyl group Chemical group 0.000 claims description 15
125000004423 acyloxy group Chemical group 0.000 claims description 15
125000003282 alkyl amino group Chemical group 0.000 claims description 15
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 15
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 15
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
125000005530 alkylenedioxy group Chemical group 0.000 claims description 15
125000005466 alkylenyl group Chemical group 0.000 claims description 15
125000003435 aroyl group Chemical group 0.000 claims description 15
125000005018 aryl alkenyl group Chemical group 0.000 claims description 15
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 15
125000001769 aryl amino group Chemical group 0.000 claims description 15
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 15
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 15
125000005421 aryl sulfonamido group Chemical group 0.000 claims description 15
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 15
125000004104 aryloxy group Chemical group 0.000 claims description 15
125000001589 carboacyl group Chemical group 0.000 claims description 15
125000004966 cyanoalkyl group Chemical group 0.000 claims description 15
125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 15
125000000000 cycloalkoxy group Chemical group 0.000 claims description 15
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
125000004967 formylalkyl group Chemical group 0.000 claims description 15
125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 15
125000001188 haloalkyl group Chemical group 0.000 claims description 15
125000004995 haloalkylthio group Chemical group 0.000 claims description 15
125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 15
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 15
125000005241 heteroarylamino group Chemical group 0.000 claims description 15
125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 15
125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 15
125000005368 heteroarylthio group Chemical group 0.000 claims description 15
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
230000009826 neoplastic cell growth Effects 0.000 claims description 15
239000011593 sulfur Substances 0.000 claims description 15
206010061218 Inflammation Diseases 0.000 claims description 14
125000004442 acylamino group Chemical group 0.000 claims description 14
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 14
230000002265 prevention Effects 0.000 claims description 14
125000005110 aryl thio group Chemical group 0.000 claims description 13
230000004054 inflammatory process Effects 0.000 claims description 13
125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 10
VQGCWTDMOOOHCH-PFPYCLJUSA-N (z,2s)-2-amino-7-(1-aminoethylideneamino)-6-fluorohept-5-enoic acid Chemical compound CC(=N)NC\C(F)=C\CC[C@H](N)C(O)=O VQGCWTDMOOOHCH-PFPYCLJUSA-N 0.000 claims description 9
VQGCWTDMOOOHCH-DKCNVOGISA-N (e,2s)-2-amino-7-(1-aminoethylideneamino)-6-fluorohept-5-enoic acid Chemical compound CC(=N)NC\C(F)=C/CC[C@H](N)C(O)=O VQGCWTDMOOOHCH-DKCNVOGISA-N 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
206010003246 arthritis Diseases 0.000 claims description 7
150000001768 cations Chemical class 0.000 claims description 7
229910052804 chromium Inorganic materials 0.000 claims description 7
210000002919 epithelial cell Anatomy 0.000 claims description 7
150000004682 monohydrates Chemical class 0.000 claims description 7
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 7
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
206010012335 Dependence Diseases 0.000 claims description 6
238000001356 surgical procedure Methods 0.000 claims description 6
VQGCWTDMOOOHCH-HOOMWESVSA-N (e,2r)-2-amino-7-(1-aminoethylideneamino)-6-fluorohept-5-enoic acid Chemical compound CC(=N)NC\C(F)=C/CC[C@@H](N)C(O)=O VQGCWTDMOOOHCH-HOOMWESVSA-N 0.000 claims description 5
229910002651 NO3 Inorganic materials 0.000 claims description 5
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
150000001450 anions Chemical class 0.000 claims description 5
201000011510 cancer Diseases 0.000 claims description 5
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 4
208000014674 injury Diseases 0.000 claims description 4
201000008482 osteoarthritis Diseases 0.000 claims description 4
210000001519 tissue Anatomy 0.000 claims description 4
206010006187 Breast cancer Diseases 0.000 claims description 3
208000026310 Breast neoplasm Diseases 0.000 claims description 3
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 3
206010008342 Cervix carcinoma Diseases 0.000 claims description 3
206010009944 Colon cancer Diseases 0.000 claims description 3
201000003883 Cystic fibrosis Diseases 0.000 claims description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 3
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
206010035664 Pneumonia Diseases 0.000 claims description 3
206010060862 Prostate cancer Diseases 0.000 claims description 3
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
201000010881 cervical cancer Diseases 0.000 claims description 3
230000006378 damage Effects 0.000 claims description 3
150000004683 dihydrates Chemical class 0.000 claims description 3
201000005202 lung cancer Diseases 0.000 claims description 3
208000020816 lung neoplasm Diseases 0.000 claims description 3
230000002980 postoperative effect Effects 0.000 claims description 3
230000002633 protecting effect Effects 0.000 claims description 3
208000011580 syndromic disease Diseases 0.000 claims description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
208000002177 Cataract Diseases 0.000 claims description 2
WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 claims description 2
208000027418 Wounds and injury Diseases 0.000 claims description 2
208000029742 colonic neoplasm Diseases 0.000 claims description 2
WHUUTDBJXJRKMK-UHFFFAOYSA-N glutamic acid Chemical compound OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 13
125000000129 anionic group Chemical group 0.000 claims 11
125000002091 cationic group Chemical group 0.000 claims 7
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 4
229910019142 PO4 Inorganic materials 0.000 claims 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 4
239000010452 phosphate Substances 0.000 claims 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims 3
150000007942 carboxylates Chemical class 0.000 claims 3
150000004820 halides Chemical class 0.000 claims 3
208000015181 infectious disease Diseases 0.000 claims 3
230000002757 inflammatory effect Effects 0.000 claims 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 3
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 3
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 3
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 3
229910052723 transition metal Inorganic materials 0.000 claims 3
GVKATAYJPTXTPD-CZEYKFRCSA-N (e,2s)-2-amino-7-(1-aminoethylideneamino)-5,6-difluorohept-5-enoic acid Chemical compound CC(=N)NC\C(F)=C(/F)CC[C@H](N)C(O)=O GVKATAYJPTXTPD-CZEYKFRCSA-N 0.000 claims 2
GVKATAYJPTXTPD-UAPHAKCISA-N (z,2s)-2-amino-7-(1-aminoethylideneamino)-5,6-difluorohept-5-enoic acid Chemical compound CC(=N)NC\C(F)=C(\F)CC[C@H](N)C(O)=O GVKATAYJPTXTPD-UAPHAKCISA-N 0.000 claims 2
NLBSQHGCGGFVJW-UHFFFAOYSA-N 2-carboxyethylphosphonic acid Chemical compound OC(=O)CCP(O)(O)=O NLBSQHGCGGFVJW-UHFFFAOYSA-N 0.000 claims 2
239000004925 Acrylic resin Substances 0.000 claims 2
RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 claims 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
KPSZWAJWFMFMFF-UHFFFAOYSA-N delta-Hexylen-alpha-carbonsaeure Natural products CC=CCCCC(O)=O KPSZWAJWFMFMFF-UHFFFAOYSA-N 0.000 claims 2
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims 2
235000019797 dipotassium phosphate Nutrition 0.000 claims 2
229910000396 dipotassium phosphate Inorganic materials 0.000 claims 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims 2
229910000397 disodium phosphate Inorganic materials 0.000 claims 2
235000019800 disodium phosphate Nutrition 0.000 claims 2
230000003211 malignant effect Effects 0.000 claims 2
239000001488 sodium phosphate Substances 0.000 claims 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
XVOYSCVBGLVSOL-UWTATZPHSA-N (2s)-2-amino-3-sulfopropanoic acid Chemical compound OC(=O)[C@H](N)CS(O)(=O)=O XVOYSCVBGLVSOL-UWTATZPHSA-N 0.000 claims 1
BJEPYKJPYRNKOW-UWTATZPHSA-N (R)-malic acid Chemical compound OC(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-N 0.000 claims 1
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 claims 1
JVTAAEKCZFNVCJ-REOHCLBHSA-M (S)-lactate Chemical compound C[C@H](O)C([O-])=O JVTAAEKCZFNVCJ-REOHCLBHSA-M 0.000 claims 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
IWYDHOAUDWTVEP-ZETCQYMHSA-N (S)-mandelic acid Chemical compound OC(=O)[C@@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-ZETCQYMHSA-N 0.000 claims 1
CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims 1
SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 claims 1
LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 claims 1
CIWBSHSKHKDKBQ-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)-3,4-dihydroxy-2h-furan-5-one Chemical compound OCC(O)C1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-UHFFFAOYSA-N 0.000 claims 1
AOTQGWFNFTVXNQ-UHFFFAOYSA-N 2-(1-adamantyl)acetic acid Chemical compound C1C(C2)CC3CC2CC1(CC(=O)O)C3 AOTQGWFNFTVXNQ-UHFFFAOYSA-N 0.000 claims 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims 1
229940080296 2-naphthalenesulfonate Drugs 0.000 claims 1
RIOSJKSGNLGONI-UHFFFAOYSA-N 2-phenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 RIOSJKSGNLGONI-UHFFFAOYSA-N 0.000 claims 1
ODHCTXKNWHHXJC-GSVOUGTGSA-N 5-oxo-D-proline Chemical compound OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims 1
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims 1
ODHCTXKNWHHXJC-UHFFFAOYSA-N 5-oxoproline Chemical compound OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
CKLJMWTZIZZHCS-UHFFFAOYSA-N Aspartic acid Chemical compound OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
CIWBSHSKHKDKBQ-MVHIGOERSA-N D-ascorbic acid Chemical compound OC[C@@H](O)[C@@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-MVHIGOERSA-N 0.000 claims 1
CKLJMWTZIZZHCS-UWTATZPHSA-N D-aspartic acid Chemical compound OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims 1
229930195713 D-glutamate Natural products 0.000 claims 1
JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims 1
FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 claims 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
XVOYSCVBGLVSOL-REOHCLBHSA-N L-cysteic acid Chemical compound OC(=O)[C@@H](N)CS(O)(=O)=O XVOYSCVBGLVSOL-REOHCLBHSA-N 0.000 claims 1
229930195714 L-glutamate Natural products 0.000 claims 1
HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims 1
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
206010040047 Sepsis Diseases 0.000 claims 1
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
241000700605 Viruses Species 0.000 claims 1
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims 1
JIMXXGFJRDUSRO-UHFFFAOYSA-M adamantane-1-carboxylate Chemical compound C1C(C2)CC3CC2CC1(C(=O)[O-])C3 JIMXXGFJRDUSRO-UHFFFAOYSA-M 0.000 claims 1
229940077388 benzenesulfonate Drugs 0.000 claims 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
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- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/10—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers

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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
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AU2001255391A 2000-04-13 2001-04-13 Halogentated 2-amino-5,6 heptenoic acid derivatives useful as nitric oxide synthase inhibitors Abandoned AU2001255391A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US19703200P	2000-04-13	2000-04-13
US60197032		2000-04-13
PCT/US2001/012258 WO2001078719A1 (en)	2000-04-13	2001-04-13	Halogentated 2-amino-5,6 heptenoic acid derivatives useful as nitric oxide synthase inhibitors

Publications (1)

Publication Number	Publication Date
AU2001255391A1 true AU2001255391A1 (en)	2001-10-30

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AU2001255391A Abandoned AU2001255391A1 (en)	2000-04-13	2001-04-13	Halogentated 2-amino-5,6 heptenoic acid derivatives useful as nitric oxide synthase inhibitors

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Country	Link
US (1)	US6465686B2 (es)
EP (1)	EP1282413A4 (es)
JP (1)	JP2003530435A (es)
KR (1)	KR20030040202A (es)
CN (1)	CN1437468A (es)
AR (1)	AR032318A1 (es)
AU (1)	AU2001255391A1 (es)
BR (1)	BR0110143A (es)
CA (1)	CA2405597A1 (es)
EA (1)	EA200201054A1 (es)
MX (1)	MXPA02010068A (es)
NZ (1)	NZ521879A (es)
WO (1)	WO2001078719A1 (es)
ZA (1)	ZA200208169B (es)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7718644B2 (en)	2004-01-22	2010-05-18	The Trustees Of Columbia University In The City Of New York	Anti-arrhythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2) and uses thereof
US7879840B2 (en)	2005-08-25	2011-02-01	The Trustees Of Columbia University In The City Of New York	Agents for preventing and treating disorders involving modulation of the RyR receptors
US7393652B2 (en)	2000-05-10	2008-07-01	The Trustees Of Columbia University In The City Of New York	Methods for identifying a chemical compound that directly enhances binding of FKBP12.6 to PKA-phosphorylated type 2 ryanodine receptor (RyR2)
US8022058B2 (en)	2000-05-10	2011-09-20	The Trustees Of Columbia University In The City Of New York	Agents for preventing and treating disorders involving modulation of the RyR receptors
US7012098B2 (en) *	2001-03-23	2006-03-14	Pharmacia Corporation	Inhibitors of inducible nitric oxide synthase for chemoprevention and treatment of cancers
WO2003022309A1 (fr) *	2001-09-10	2003-03-20	Ono Pharmaceutical Co., Ltd.	Remedes pour maladies allergiques
US20030109522A1 (en) *	2001-09-24	2003-06-12	Manning Pamela T.	Ophthalmologic treatment methods using selective iNOS inhibitors
US20030119826A1 (en) *	2001-09-24	2003-06-26	Pharmacia Corporation	Neuroprotective treatment methods using selective iNOS inhibitors
IL164826A0 (en) *	2002-05-16	2005-12-18	Pharmacia Corp	Methods for the treatment of respiratory diseases and conditions using a selective inos inhibitor
BR0310061A (pt) *	2002-05-16	2005-03-01	Pharmacia Corp	Métodos para o tratamento de doenças e condições respiratórias com um inibidor seletivo da inos e um inibidor da pde e suas composições
ES2307102T3 (es) *	2002-06-19	2008-11-16	Biovitrum Ab (Publ)	Piperazinilpirazinas como moduladores del receptor de la serotonina 5-ht2c.
EP1528921A2 (en) *	2002-08-02	2005-05-11	Pharmacia Corporation	Methods for treatment and prevention of gastrointestinal conditions
US7544678B2 (en)	2002-11-05	2009-06-09	The Trustees Of Columbia University In The City Of New York	Anti-arrythmic and heart failure drugs that target the leak in the ryanodine receptor (RyR2)
JP2007525165A (ja)	2003-03-07	2007-09-06	トラスティーズ・オブ・コロンビア・ユニバーシティ・イン・ザ・シティ・オブ・ニューヨーク	タイプ１ライアノジン受容体に基づく方法
WO2005025620A2 (en) *	2003-08-13	2005-03-24	Pharmacia Corporation	Combination therapy with inhibitors of inducible nitric oxide synthase and alkylating agents
US8710045B2 (en)	2004-01-22	2014-04-29	The Trustees Of Columbia University In The City Of New York	Agents for preventing and treating disorders involving modulation of the ryanodine receptors
WO2005110396A2 (en)	2004-04-28	2005-11-24	Uab Research Foundation	Nitrated lipids and methods of making and using thereof
US7704990B2 (en)	2005-08-25	2010-04-27	The Trustees Of Columbia University In The City Of New York	Agents for preventing and treating disorders involving modulation of the RyR receptors
EP2679224A1 (en)	2007-08-01	2014-01-01	University of Pittsburgh of the Commonwealth System of Higher Education	Nitro oleic acid modulation of type II diabetes
CN102083787A (zh)	2008-05-01	2011-06-01	康普雷克萨公司	乙烯基取代的脂肪酸
US8686038B2 (en)	2008-06-19	2014-04-01	The Univsersity of Utah Research Foundation	Use of nitrated lipids for treatment of side effects of toxic medical therapies
US20140024713A1 (en)	2008-06-19	2014-01-23	University Of Utah Research Foundation	Use of nitrated lipids for treatment of side effects of toxic medical therapies
US9066902B2 (en)	2009-07-31	2015-06-30	University of Pittsburgh—of the Commonwealth System of Higher Education	Fatty acids as anti-inflammatory agents
US8686167B2 (en)	2009-10-02	2014-04-01	Complexa, Inc.	Heteroatom containing substituted fatty acids
EP2322514A1 (en) *	2009-11-11	2011-05-18	Bayer Schering Pharma Aktiengesellschaft	Homoglutamic acid and glutamic acid derivatives
WO2013028501A1 (en)	2011-08-19	2013-02-28	The University Of Utah Research Foundation	Combination therapy with nitrated lipids and inhibitors of the renin-angiotensin-aldosterone system
EP2687511A1 (de) *	2012-07-17	2014-01-22	Zedira GmbH	Pyridinonderivate als Gewebetransglutaminaseinhibitoren
MX379456B (es)	2015-07-07	2025-03-10	H Lundbeck As	Inhibidores de fde9 con estructura básica de imidazotriazinona y estructura básica de imidazopirazinona en el tratamiento de enfermedades periféricas.
SG10201913953UA (en)	2015-10-02	2020-03-30	Complexa Inc	Prevention, treatment and reversal of disease using therapeutically effective amounts of activated fatty acids
CA3100988A1 (en)	2018-05-25	2019-11-28	Imara Inc.	Monohydrate and crystalline forms of 6-[(3s,4s)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-3-tetrahydropyran-4-yl-7h-imidazo[1,5-a]pyrazin-8-one
WO2020047311A1 (en)	2018-08-31	2020-03-05	Imara Inc.	Pde9 inhibitors for treating sickle cell disease
CN109021061B (zh) *	2018-09-29	2019-07-12	郭可点	雷公藤甲素靶向前药及其制备方法和应用

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2036770C (en)	1990-02-26	2003-09-09	Jeffrey P. Whitten	Inhibitors of nitric oxide biosynthesis
US5132453A (en)	1991-03-22	1992-07-21	Cornell Research Foundation, Inc.	N6 -(hydrazinoiminomethyl)lysine and method of inhibiting nitric oxide formation in body
JP2648897B2 (ja)	1991-07-01	1997-09-03	塩野義製薬株式会社	ピリミジン誘導体
GB9127376D0 (en)	1991-12-24	1992-02-19	Wellcome Found	Amidino derivatives
GB9203347D0 (en)	1992-02-17	1992-04-01	Wellcome Found	Hypolipidaemic compounds
SI9300616A (en)	1992-11-27	1994-06-30	Wellcome Found	Enzyme inhibitors
AU5704594A (en)	1992-12-18	1994-07-19	Wellcome Foundation Limited, The	Pyrimidine, pyridine, pteridinone and indazole derivatives as enzyme inhibitors
US5821267A (en)	1993-10-21	1998-10-13	G.D. Searle & Co.	Amidino derivatives useful as nitric oxide synthase inhibitors
JPH09504028A (ja)	1993-10-21	1997-04-22	ジー．ディー．サールアンドカンパニー	酸化窒素シンターゼ抑制剤として有用なアミジノ誘導体
WO1995024382A1 (en) *	1994-03-10	1995-09-14	G.D. Searle & Co.	L-n6-(1-iminoethyl)lysine derivatives useful as nitric oxide synthase inhibitors
ATE188467T1 (de) *	1994-03-24	2000-01-15	Searle & Co	Amidino-derivative als no-synthese-inhibitoren
US5994391A (en)	1994-09-13	1999-11-30	G.D. Searle And Company	Benzothiepines having activity as inhibitors of ileal bile acid transport and taurocholate uptake
US5684008A (en)	1994-11-09	1997-11-04	G. D. Searle & Co.	Aminotetrazole derivatives useful as nitric oxide synthase inhibitors
US6011028A (en)	1995-04-20	2000-01-04	G.D. Searle & Co.	Cyclic amidino agents useful as nitric oxide synthase inhibitors
BR9608133A (pt)	1995-05-10	1999-02-09	Searle & Co	Inibidores da sintase de óxido nítrico derivados de amidinas cíclas
GB9516709D0 (en)	1995-08-15	1995-10-18	Zeneca Ltd	Medicament
US5830917A (en)	1995-09-11	1998-11-03	G. D. Searle & Co.	L-N6 -(1-iminoethyl) lysine derivatives useful as nitric oxide synthase inhibitors
US5981511A (en)	1996-03-06	1999-11-09	G.D. Searle & Co.	Hydroxyamidino derivatives useful as nitric oxide synthase inhibitors
US5945408A (en) *	1996-03-06	1999-08-31	G.D. Searle & Co.	Hydroxyanidino derivatives useful as nitric oxide synthase inhibitors
WO1999029865A2 (en)	1997-12-12	1999-06-17	The Rockefeller University	A protein belonging to the tnf superfamily, nucleic acids encoding same, and methods of use thereof
US6344483B1 (en)	1998-03-11	2002-02-05	G. D. Searle & Co.	Halogenated amidino amino acid deviratives useful as nitric oxide synthase inhibitors
MY131964A (en) *	2000-09-15	2007-09-28	Pharmacia Corp	2-amino-2-alkyl-5 heptenoic and heptynoic acid derivatives useful as nitric oxide synthase inhibitors

2001
- 2001-04-11 AR ARP010101735A patent/AR032318A1/es unknown
- 2001-04-13 EA EA200201054A patent/EA200201054A1/ru unknown
- 2001-04-13 US US09/835,191 patent/US6465686B2/en not_active Expired - Fee Related
- 2001-04-13 CN CN01810938A patent/CN1437468A/zh active Pending
- 2001-04-13 BR BR0110143-9A patent/BR0110143A/pt not_active IP Right Cessation
- 2001-04-13 NZ NZ52187901A patent/NZ521879A/xx unknown
- 2001-04-13 JP JP2001576019A patent/JP2003530435A/ja not_active Withdrawn
- 2001-04-13 WO PCT/US2001/012258 patent/WO2001078719A1/en not_active Ceased
- 2001-04-13 KR KR1020027013747A patent/KR20030040202A/ko not_active Withdrawn
- 2001-04-13 MX MXPA02010068A patent/MXPA02010068A/es active IP Right Grant
- 2001-04-13 AU AU2001255391A patent/AU2001255391A1/en not_active Abandoned
- 2001-04-13 EP EP01928544A patent/EP1282413A4/en not_active Withdrawn
- 2001-04-13 CA CA002405597A patent/CA2405597A1/en not_active Abandoned
2002
- 2002-10-10 ZA ZA200208169A patent/ZA200208169B/en unknown

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Publication number	Publication date
ZA200208169B (en)	2003-10-10
EP1282413A1 (en)	2003-02-12
US6465686B2 (en)	2002-10-15
KR20030040202A (ko)	2003-05-22
NZ521879A (en)	2004-12-24
MXPA02010068A (es)	2003-09-10
BR0110143A (pt)	2005-01-11
EP1282413A4 (en)	2004-12-01
AR032318A1 (es)	2003-11-05
WO2001078719A1 (en)	2001-10-25
US20020049202A1 (en)	2002-04-25
EA200201054A1 (ru)	2003-06-26
CN1437468A (zh)	2003-08-20
CA2405597A1 (en)	2001-10-25
JP2003530435A (ja)	2003-10-14

Publication	Publication Date	Title
US6465686B2 (en)	2002-10-15	Halogenated 2-amino-5,6 heptenoic acid derivatives useful as nitric oxide synthase inhibitors
US6545170B2 (en)	2003-04-08	2-amino-5, 6 heptenoic acid derivatives useful as nitric oxide synthase inhibitors
EP1265859B1 (en)	2005-12-21	Amidino compounds useful as nitric oxide synthase inhibitors
US6465518B2 (en)	2002-10-15	Halogenated 2-amino-4, 5 heptenoic acid derivatives useful as nitric oxide synthase inhibitors
EP1317421B1 (en)	2005-02-23	2-amino-2-alkyl-5 heptenoic and heptynoic acid derivatives useful as nitric oxide synthase inhibitors
AU2001249415A1 (en)	2001-12-20	Amidino compound and salts thereof useful as nitric oxide synthase inhibitors
CA2420007A1 (en)	2002-03-21	2-amino-2-alkyl-4 hexenoic and hexynoic acid derivatives useful as nitric oxide synthase inhibitors
US6586471B1 (en)	2003-07-01	Halogenated 2-amino-3, 4 heptenoic acid derivatives useful as nitric oxide synthase inhibitors
US6787668B2 (en)	2004-09-07	2-amino-4,5 heptenoic acid derivatives useful as nitric oxide synthase inhibitors
US6828456B2 (en)	2004-12-07	2-amino-2-alkyl-3 hexenoic and hexynoic acid derivatives useful as nitric oxide synthase inhibitors
US20020103398A1 (en)	2002-08-01	2-Amino-2-alky-4 heptenoic and heptynoic acid derivatives useful as nitric oxide synthase inhibitors
US20020072630A1 (en)	2002-06-13	2-amino-2-alkyl-3 heptenoic and heptynoic acid derivatives useful as nitric oxide synthase inhibitors
HK1050521B (en)	2006-05-12	Amidino compounds useful as nitric oxide synthase inhibitors