JP2003513002A5 - - Google Patents
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- Publication number
- JP2003513002A5 JP2003513002A5 JP2000549576A JP2000549576A JP2003513002A5 JP 2003513002 A5 JP2003513002 A5 JP 2003513002A5 JP 2000549576 A JP2000549576 A JP 2000549576A JP 2000549576 A JP2000549576 A JP 2000549576A JP 2003513002 A5 JP2003513002 A5 JP 2003513002A5
- Authority
- JP
- Japan
- Prior art keywords
- trimethylammonium
- group
- aminobutyrate
- alkyl
- pharmaceutical composition
- 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 description 17
- 239000008194 pharmaceutical composition Substances 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- -1 tetrazole benzoate Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 5
- 206010012601 diabetes mellitus Diseases 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- 208000008589 Obesity Diseases 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 235000020824 obesity Nutrition 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 229940123324 Acyltransferase inhibitor Drugs 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 description 2
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 description 2
- 108010054082 Sterol O-acyltransferase Proteins 0.000 description 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
- 239000002404 acyltransferase inhibitor Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940125753 fibrate Drugs 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
- RWIUTHWKQHRQNP-ZDVGBALWSA-N (9e,12e)-n-(1-phenylethyl)octadeca-9,12-dienamide Chemical compound CCCCC\C=C\C\C=C\CCCCCCCC(=O)NC(C)C1=CC=CC=C1 RWIUTHWKQHRQNP-ZDVGBALWSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-O 1-azoniabicyclo[2.2.2]octane Chemical compound C1CC2CC[NH+]1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-O 0.000 description 1
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 description 1
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 1
- SHGAZHPCJJPHSC-ZVCIMWCZSA-N 9-cis-retinoic acid Chemical compound OC(=O)/C=C(\C)/C=C/C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-ZVCIMWCZSA-N 0.000 description 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 1
- 229940123413 Angiotensin II antagonist Drugs 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 102000002666 Carnitine O-palmitoyltransferase Human genes 0.000 description 1
- 108010018424 Carnitine O-palmitoyltransferase Proteins 0.000 description 1
- 229920001268 Cholestyramine Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010088406 Glucagon-Like Peptides Proteins 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 229940122199 Insulin secretagogue Drugs 0.000 description 1
- 101710190529 Insulin-like peptide Proteins 0.000 description 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- 108010016731 PPAR gamma Proteins 0.000 description 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229960001445 alitretinoin Drugs 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001548 androgenic effect Effects 0.000 description 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940076810 beta sitosterol Drugs 0.000 description 1
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 1
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical group 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- 229960004597 dexfenfluramine Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- 229960001582 fenfluramine Drugs 0.000 description 1
- 239000002319 fibrinogen receptor antagonist Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- MGXWVYUBJRZYPE-YUGYIWNOSA-N incretin Chemical class C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)[C@@H](C)O)[C@@H](C)CC)C1=CC=C(O)C=C1 MGXWVYUBJRZYPE-YUGYIWNOSA-N 0.000 description 1
- 239000000859 incretin Substances 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229950008446 melinamide Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-O morpholinium Chemical compound [H+].C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-O 0.000 description 1
- 229960004738 nicotinyl alcohol Drugs 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 125000003441 thioacyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000000929 thyromimetic effect Effects 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940126158 β3 adrenergic receptor agonist Drugs 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI98A001075 | 1998-05-15 | ||
| IT98A001075 | 1998-05-15 | ||
| IT98MI001075A IT1299266B1 (it) | 1998-05-15 | 1998-05-15 | Inibitori reversibili della carnitina palmitoil trasferasi |
| PCT/IT1999/000126 WO1999059957A1 (en) | 1998-05-15 | 1999-05-11 | Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003513002A JP2003513002A (ja) | 2003-04-08 |
| JP2003513002A5 true JP2003513002A5 (OSRAM) | 2006-07-27 |
| JP5127093B2 JP5127093B2 (ja) | 2013-01-23 |
Family
ID=11380036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000549576A Expired - Fee Related JP5127093B2 (ja) | 1998-05-15 | 1999-05-11 | カルニチンパルミトイル−トランスフェラーゼの可逆的阻害活性を有する化合物 |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US6369073B1 (OSRAM) |
| EP (2) | EP1077925B1 (OSRAM) |
| JP (1) | JP5127093B2 (OSRAM) |
| KR (1) | KR100585443B1 (OSRAM) |
| AT (2) | ATE465988T1 (OSRAM) |
| AU (1) | AU3847399A (OSRAM) |
| CA (1) | CA2329930C (OSRAM) |
| CY (1) | CY1110200T1 (OSRAM) |
| DE (2) | DE69920208T2 (OSRAM) |
| DK (2) | DK1077925T3 (OSRAM) |
| ES (2) | ES2230854T3 (OSRAM) |
| IT (1) | IT1299266B1 (OSRAM) |
| PT (2) | PT1484313E (OSRAM) |
| WO (1) | WO1999059957A1 (OSRAM) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1299266B1 (it) | 1998-05-15 | 2000-02-29 | Sigma Tau Ind Farmaceuti | Inibitori reversibili della carnitina palmitoil trasferasi |
| US6822115B2 (en) * | 1999-06-30 | 2004-11-23 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid |
| IT1317885B1 (it) * | 2000-08-01 | 2003-07-15 | Sigma Tau Ind Farmaceuti | Uso di fibrati per la preparazione di un medicamento utile neltrattamento dell'insufficienza cardiaca congestizia. |
| ITRM20010456A1 (it) * | 2001-07-26 | 2003-01-27 | Sigma Tau Ind Farmaceuti | Procedimento per la preparazione di (r)- o (s)- amminocarnitina sale interno, dei suoi sali e dei suoi derivati. |
| US7045547B2 (en) * | 2002-08-20 | 2006-05-16 | University Of Delaware | Acyl-CoA dehydrogenase allenic inhibitors |
| ITRM20030053A1 (it) * | 2003-02-10 | 2004-08-11 | Sigma Tau Ind Farmaceuti | Associazione di farmaci antidiabetici. |
| WO2004071458A2 (en) * | 2003-02-13 | 2004-08-26 | Albert Einstein College Of Medicine Of Yeshiva University | REGULATION OF FOOD INTAKE AND GLUCOSE PRODUCTION BY MODULATION OF LONG-CHAIN FATTY ACYL-CoA LEVELS IN THE HYPOTHALAMUS |
| US7041286B2 (en) * | 2003-07-23 | 2006-05-09 | Nerenberg Arnold P | Composition for mitigating a pernicious thrombotic event |
| US8314144B2 (en) | 2004-02-12 | 2012-11-20 | Defiante Farmaceutica, S.A. | Compounds having antitumor activity |
| ITMI20040230A1 (it) | 2004-02-12 | 2004-05-12 | Defiante Farmaceutica Lda | Composti ad attivita' antitumorale |
| WO2006041922A2 (en) * | 2004-10-08 | 2006-04-20 | Dara Biosciences, Inc. | Agents and methods for administration to the central nervous system |
| WO2006088875A2 (en) * | 2005-02-14 | 2006-08-24 | Albert Einstein College Of Medicine Of Yeshiva University | Intranasal administration of modulators of hypothalamic atp-sensitive potassium channels |
| ITRM20050090A1 (it) * | 2005-03-02 | 2006-09-03 | Sigma Tau Ind Farmaceutiche Riunite Spa | Derivati dell'acido ammino-butanoico inibitore della cpt. |
| ES2342842T3 (es) * | 2005-06-06 | 2010-07-15 | F. Hoffmann-La Roche Ag | Derivados de sulfamida utiles como inhibidores de la carniti-na-palmitoil-transferasa de higado (l-cpt1). |
| KR20090034969A (ko) * | 2006-08-02 | 2009-04-08 | 시그마타우 인두스트리에 파르마슈티케 리우니테 에스.피.에이. | 씨피티-억제제로서 4-트라이메틸암모늄-3-아미노부티레이트및 4-트라이메틸포스포늄-3-아미노부티레이트의 유도체 |
| CA2680366C (en) * | 2007-03-09 | 2016-06-21 | University Health Network | Inhibitors of carnitine palmitoyltransferase and treating cancer |
| WO2009002433A1 (en) * | 2007-06-22 | 2008-12-31 | Dara Biosciences, Inc. | Compositions and methods for treating skin disorders |
| CA2677049A1 (en) * | 2007-08-01 | 2009-02-05 | Sionex Corporation | Cyclic inhibitors of carnitine palmitoyltransferase and treating cancer |
| EP2183214A1 (en) * | 2007-08-07 | 2010-05-12 | SIGMA-TAU Industrie Farmaceutiche Riunite S.p.A. | Crystalline teglicar |
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-
1998
- 1998-05-15 IT IT98MI001075A patent/IT1299266B1/it active IP Right Grant
-
1999
- 1999-05-11 ES ES99921135T patent/ES2230854T3/es not_active Expired - Lifetime
- 1999-05-11 DK DK99921135T patent/DK1077925T3/da active
- 1999-05-11 AU AU38473/99A patent/AU3847399A/en not_active Abandoned
- 1999-05-11 JP JP2000549576A patent/JP5127093B2/ja not_active Expired - Fee Related
- 1999-05-11 KR KR1020007012826A patent/KR100585443B1/ko not_active Expired - Fee Related
- 1999-05-11 AT AT04009193T patent/ATE465988T1/de active
- 1999-05-11 EP EP99921135A patent/EP1077925B1/en not_active Expired - Lifetime
- 1999-05-11 DK DK04009193.6T patent/DK1484313T3/da active
- 1999-05-11 WO PCT/IT1999/000126 patent/WO1999059957A1/en not_active Ceased
- 1999-05-11 AT AT99921135T patent/ATE276230T1/de active
- 1999-05-11 PT PT04009193T patent/PT1484313E/pt unknown
- 1999-05-11 CA CA2329930A patent/CA2329930C/en not_active Expired - Fee Related
- 1999-05-11 ES ES04009193T patent/ES2345100T3/es not_active Expired - Lifetime
- 1999-05-11 EP EP04009193A patent/EP1484313B1/en not_active Expired - Lifetime
- 1999-05-11 DE DE69920208T patent/DE69920208T2/de not_active Expired - Lifetime
- 1999-05-11 DE DE69942315T patent/DE69942315D1/de not_active Expired - Lifetime
- 1999-05-11 PT PT99921135T patent/PT1077925E/pt unknown
-
2000
- 2000-10-02 US US09/677,328 patent/US6369073B1/en not_active Ceased
-
2001
- 2001-11-08 US US09/986,327 patent/US6444701B1/en not_active Ceased
-
2006
- 2006-11-30 US US11/606,322 patent/USRE40861E1/en not_active Expired - Lifetime
- 2006-12-01 US US11/607,078 patent/USRE41226E1/en not_active Expired - Fee Related
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2010
- 2010-07-13 CY CY20101100655T patent/CY1110200T1/el unknown
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