OA12050A - Certain alkylene diamine-substituted heterocycles. - Google Patents
Certain alkylene diamine-substituted heterocycles. Download PDFInfo
- Publication number
- OA12050A OA12050A OA1200200089A OA1200200089A OA12050A OA 12050 A OA12050 A OA 12050A OA 1200200089 A OA1200200089 A OA 1200200089A OA 1200200089 A OA1200200089 A OA 1200200089A OA 12050 A OA12050 A OA 12050A
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- OA
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- Prior art keywords
- methylene
- compound
- formula
- hydrogen
- alkyl
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- 125000000623 heterocyclic group Chemical class 0.000 title claims description 28
- 125000002947 alkylene group Chemical group 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 565
- -1 eating disorders Chemical compound 0.000 claims abstract description 497
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 70
- 239000000203 mixture Substances 0.000 claims abstract description 68
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
- 125000001424 substituent group Chemical group 0.000 claims abstract description 34
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 27
- 101710151321 Melanostatin Proteins 0.000 claims abstract description 23
- 125000004429 atom Chemical group 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 6
- 208000008589 Obesity Diseases 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 235000020824 obesity Nutrition 0.000 claims abstract description 6
- 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 5
- 208000030814 Eating disease Diseases 0.000 claims abstract description 5
- 208000032841 Bulimia Diseases 0.000 claims abstract description 4
- 206010020772 Hypertension Diseases 0.000 claims abstract description 4
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 102400000064 Neuropeptide Y Human genes 0.000 claims abstract 10
- 125000006413 ring segment Chemical group 0.000 claims abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 340
- 239000001257 hydrogen Substances 0.000 claims description 324
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 148
- 125000000217 alkyl group Chemical group 0.000 claims description 143
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 58
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 56
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 53
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 229910052721 tungsten Inorganic materials 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000001188 haloalkyl group Chemical group 0.000 claims description 29
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 230000027455 binding Effects 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 239000000651 prodrug Substances 0.000 claims description 21
- 229940002612 prodrug Drugs 0.000 claims description 21
- 208000035475 disorder Diseases 0.000 claims description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 16
- 125000003386 piperidinyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 239000003981 vehicle Substances 0.000 claims description 14
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 238000000338 in vitro Methods 0.000 claims description 9
- 239000000556 agonist Substances 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 8
- 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 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 230000002159 abnormal effect Effects 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 235000012631 food intake Nutrition 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 229940088597 hormone Drugs 0.000 claims description 5
- 239000005556 hormone Substances 0.000 claims description 5
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 102000004877 Insulin Human genes 0.000 claims description 4
- 108090001061 Insulin Proteins 0.000 claims description 4
- 206010047163 Vasospasm Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 230000037406 food intake Effects 0.000 claims description 4
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
- 229940125396 insulin Drugs 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000001356 surgical procedure Methods 0.000 claims description 4
- 230000000929 thyromimetic effect Effects 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 230000020595 eating behavior Effects 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 230000004899 motility Effects 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 210000002569 neuron Anatomy 0.000 claims description 3
- 239000002660 neuropeptide Y receptor antagonist Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 3
- 230000035939 shock Effects 0.000 claims description 3
- 230000002889 sympathetic effect Effects 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 108010051696 Growth Hormone Proteins 0.000 claims description 2
- 208000032843 Hemorrhage Diseases 0.000 claims description 2
- 206010061216 Infarction Diseases 0.000 claims description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
- 206010049418 Sudden Cardiac Death Diseases 0.000 claims description 2
- 206010046543 Urinary incontinence Diseases 0.000 claims description 2
- 208000022531 anorexia Diseases 0.000 claims description 2
- 206010003119 arrhythmia Diseases 0.000 claims description 2
- 230000006793 arrhythmia Effects 0.000 claims description 2
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 2
- 230000006399 behavior Effects 0.000 claims description 2
- 210000004204 blood vessel Anatomy 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 210000004351 coronary vessel Anatomy 0.000 claims description 2
- 206010061428 decreased appetite Diseases 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004427 diamine group Chemical group 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 239000000122 growth hormone Substances 0.000 claims description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
- 230000001771 impaired effect Effects 0.000 claims description 2
- 230000007574 infarction Effects 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 208000030159 metabolic disease Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 230000020341 sensory perception of pain Effects 0.000 claims description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 645
- 150000002431 hydrogen Chemical group 0.000 claims 283
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 19
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 15
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 3
- 230000001850 reproductive effect Effects 0.000 claims 2
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- NKOHRVBBQISBSB-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(O)=CC=C1CC1C(=O)NC(=O)S1 NKOHRVBBQISBSB-UHFFFAOYSA-N 0.000 claims 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
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- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- 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
- C07D215/38—Nitrogen atoms
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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- C07D473/32—Nitrogen atom
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- C07D495/04—Ortho-condensed systems
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
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US15687099P | 1999-09-30 | 1999-09-30 |
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OA12050A true OA12050A (en) | 2006-05-02 |
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OA1200200089A OA12050A (en) | 1999-09-30 | 2000-09-29 | Certain alkylene diamine-substituted heterocycles. |
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US (3) | US6506762B1 (fr) |
EP (1) | EP1224187B1 (fr) |
JP (2) | JP2003510327A (fr) |
KR (1) | KR20020043223A (fr) |
CN (1) | CN1377356A (fr) |
AT (1) | ATE318267T1 (fr) |
AU (1) | AU7738000A (fr) |
BG (1) | BG106508A (fr) |
CA (1) | CA2379640C (fr) |
CZ (1) | CZ20021086A3 (fr) |
DE (1) | DE60026155T2 (fr) |
EA (1) | EA200200424A1 (fr) |
ES (1) | ES2258476T3 (fr) |
HU (1) | HUP0202636A3 (fr) |
IL (1) | IL148903A0 (fr) |
NO (1) | NO20021358L (fr) |
NZ (1) | NZ517575A (fr) |
OA (1) | OA12050A (fr) |
PL (1) | PL354784A1 (fr) |
WO (1) | WO2001023389A2 (fr) |
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- 2000-09-29 AU AU77380/00A patent/AU7738000A/en not_active Abandoned
- 2000-09-29 KR KR1020027004150A patent/KR20020043223A/ko not_active Application Discontinuation
- 2000-09-29 HU HU0202636A patent/HUP0202636A3/hu unknown
- 2000-09-29 DE DE60026155T patent/DE60026155T2/de not_active Expired - Fee Related
- 2000-09-29 NZ NZ517575A patent/NZ517575A/en unknown
- 2000-09-29 CN CN00813704A patent/CN1377356A/zh active Pending
- 2000-09-29 PL PL00354784A patent/PL354784A1/xx not_active Application Discontinuation
- 2000-09-29 EP EP00967133A patent/EP1224187B1/fr not_active Expired - Lifetime
- 2000-09-29 IL IL14890300A patent/IL148903A0/xx unknown
- 2000-09-29 EA EA200200424A patent/EA200200424A1/ru unknown
- 2000-09-29 CZ CZ20021086A patent/CZ20021086A3/cs unknown
- 2000-09-29 JP JP2001526541A patent/JP2003510327A/ja active Pending
- 2000-09-29 WO PCT/US2000/026886 patent/WO2001023389A2/fr active IP Right Grant
- 2000-09-29 AT AT00967133T patent/ATE318267T1/de not_active IP Right Cessation
- 2000-09-29 OA OA1200200089A patent/OA12050A/en unknown
- 2000-09-29 CA CA002379640A patent/CA2379640C/fr not_active Expired - Fee Related
- 2000-09-29 ES ES00967133T patent/ES2258476T3/es not_active Expired - Lifetime
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CZ20021086A3 (cs) | 2002-10-16 |
NO20021358D0 (no) | 2002-03-19 |
IL148903A0 (en) | 2002-09-12 |
HUP0202636A2 (hu) | 2002-12-28 |
US20040229870A1 (en) | 2004-11-18 |
ES2258476T3 (es) | 2006-09-01 |
US7074929B2 (en) | 2006-07-11 |
CA2379640A1 (fr) | 2001-04-05 |
DE60026155D1 (de) | 2006-04-27 |
EA200200424A1 (ru) | 2002-12-26 |
NO20021358L (no) | 2002-05-27 |
BG106508A (en) | 2003-02-28 |
US6696445B2 (en) | 2004-02-24 |
WO2001023389A3 (fr) | 2002-05-10 |
JP2003510327A (ja) | 2003-03-18 |
CA2379640C (fr) | 2006-11-28 |
DE60026155T2 (de) | 2006-08-10 |
CN1377356A (zh) | 2002-10-30 |
EP1224187B1 (fr) | 2006-02-22 |
WO2001023389A2 (fr) | 2001-04-05 |
ZA200202518B (en) | 2003-08-27 |
PL354784A1 (en) | 2004-02-23 |
US6506762B1 (en) | 2003-01-14 |
US20030158197A1 (en) | 2003-08-21 |
ATE318267T1 (de) | 2006-03-15 |
KR20020043223A (ko) | 2002-06-08 |
JP2008007515A (ja) | 2008-01-17 |
NZ517575A (en) | 2004-04-30 |
HUP0202636A3 (en) | 2004-06-28 |
EP1224187A2 (fr) | 2002-07-24 |
AU7738000A (en) | 2001-04-30 |
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