TW200418773A - Substituted tetralins and indanes - Google Patents

Substituted tetralins and indanes Download PDF

Info

Publication number: TW200418773A
Authority: TW; Taiwan
Prior art keywords: acid; ylsulfanyl; ethyl; ureido; compound
Prior art date: 2002-10-21

Application number

TW092129192A

Other languages

English (en)

Chinese (zh)

Inventor

Xiaoli Chen

Keith T Demarest

Lee Jung

Jay M Matthews

Philip J Rybczynski

Original Assignee

Janssen Pharmaceutica Nv

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.)

2002-10-21

Filing date

2003-10-21

Publication date

2004-10-01

2003-10-21 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2004-10-01 Publication of TW200418773A publication Critical patent/TW200418773A/zh

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125000003392 indanyl group Chemical class C1(CCC2=CC=CC=C12)* 0.000 title abstract 2
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 title description 3
238000000034 method Methods 0.000 claims abstract description 32
239000000203 mixture Substances 0.000 claims abstract description 27
208000032928 Dyslipidaemia Diseases 0.000 claims abstract 4
208000017170 Lipid metabolism disease Diseases 0.000 claims abstract 4
150000001875 compounds Chemical class 0.000 claims description 232
-1 NRUR12 Chemical group 0.000 claims description 216
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 71
125000000217 alkyl group Chemical group 0.000 claims description 57
239000002253 acid Substances 0.000 claims description 49
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 43
125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 42
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
230000002079 cooperative effect Effects 0.000 claims description 35
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 27
150000002148 esters Chemical class 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
150000001412 amines Chemical class 0.000 claims description 17
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
125000005842 heteroatom Chemical group 0.000 claims description 16
239000003795 chemical substances by application Substances 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
239000008280 blood Substances 0.000 claims description 14
210000004369 blood Anatomy 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 12
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
235000019260 propionic acid Nutrition 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
150000002430 hydrocarbons Chemical group 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
125000002124 5'-adenosyl group Chemical group N1=CN=C2N(C=NC2=C1N)[C@H]1[C@H](O)[C@H](O)[C@H](O1)C* 0.000 claims description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 5
206010003210 Arteriosclerosis Diseases 0.000 claims description 5
OBAXVFVUSUVXMM-UHFFFAOYSA-N C12=CC=CC=C2CC2=C1C=CC=C2C(C(O)=O)C Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2C(C(O)=O)C OBAXVFVUSUVXMM-UHFFFAOYSA-N 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
230000001105 regulatory effect Effects 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
239000003524 antilipemic agent Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 3
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
208000029078 coronary artery disease Diseases 0.000 claims description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
235000013336 milk Nutrition 0.000 claims description 3
239000008267 milk Substances 0.000 claims description 3
210000004080 milk Anatomy 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
VTCXTXLWJYLPAB-UHFFFAOYSA-N 2-methyl-2-(1,2,3,4-tetrahydronaphthalen-2-ylsulfanyl)propanoic acid Chemical compound C1C(CCC2=CC=CC=C12)SC(C(=O)O)(C)C VTCXTXLWJYLPAB-UHFFFAOYSA-N 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
206010020772 Hypertension Diseases 0.000 claims description 2
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
238000010586 diagram Methods 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 2
235000021286 stilbenes Nutrition 0.000 claims description 2
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 2
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
208000031226 Hyperlipidaemia Diseases 0.000 claims 3
208000024172 Cardiovascular disease Diseases 0.000 claims 2
125000004414 alkyl thio group Chemical group 0.000 claims 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 claims 2
125000004404 heteroalkyl group Chemical group 0.000 claims 2
125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims 1
239000004098 Tetracycline Substances 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
239000013256 coordination polymer Substances 0.000 claims 1
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 1
229940069417 doxy Drugs 0.000 claims 1
HALQELOKLVRWRI-VDBOFHIQSA-N doxycycline hyclate Chemical group O.[Cl-].[Cl-].CCO.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O HALQELOKLVRWRI-VDBOFHIQSA-N 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
235000012054 meals Nutrition 0.000 claims 1
230000001404 mediated effect Effects 0.000 claims 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
229960002180 tetracycline Drugs 0.000 claims 1
229930101283 tetracycline Natural products 0.000 claims 1
235000019364 tetracycline Nutrition 0.000 claims 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract description 12
102000023984 PPAR alpha Human genes 0.000 abstract 1
108010028924 PPAR alpha Proteins 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 126
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 79
239000007787 solid Substances 0.000 description 70
239000000243 solution Substances 0.000 description 55
239000002904 solvent Substances 0.000 description 46
230000002829 reductive effect Effects 0.000 description 40
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
238000005481 NMR spectroscopy Methods 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
101150041968 CDC13 gene Proteins 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
235000002639 sodium chloride Nutrition 0.000 description 21
238000003818 flash chromatography Methods 0.000 description 20
238000012360 testing method Methods 0.000 description 20
239000003921 oil Substances 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 18
229910052681 coesite Inorganic materials 0.000 description 18
229910052906 cristobalite Inorganic materials 0.000 description 18
229910052682 stishovite Inorganic materials 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
229910052905 tridymite Inorganic materials 0.000 description 18
125000003118 aryl group Chemical group 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
229910052938 sodium sulfate Inorganic materials 0.000 description 16
235000011152 sodium sulphate Nutrition 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 14
210000002966 serum Anatomy 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000000284 extract Substances 0.000 description 12
239000000725 suspension Substances 0.000 description 12
239000003153 chemical reaction reagent Substances 0.000 description 11
235000019439 ethyl acetate Nutrition 0.000 description 11
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 11
239000002609 medium Substances 0.000 description 11
235000021419 vinegar Nutrition 0.000 description 11
101150014691 PPARA gene Proteins 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 10
239000000377 silicon dioxide Substances 0.000 description 10
235000012239 silicon dioxide Nutrition 0.000 description 10
LGPKFIGMLPDYEA-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethoxy)benzene Chemical group FC(F)(F)OC1=CC=C(N=C=O)C=C1 LGPKFIGMLPDYEA-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000000556 agonist Substances 0.000 description 9
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 9
239000012267 brine Substances 0.000 description 9
239000003814 drug Substances 0.000 description 9
125000000623 heterocyclic group Chemical group 0.000 description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 8
239000012346 acetyl chloride Substances 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
150000002170 ethers Chemical class 0.000 description 8
239000007789 gas Substances 0.000 description 8
239000012948 isocyanate Substances 0.000 description 8
150000002632 lipids Chemical class 0.000 description 8
230000037361 pathway Effects 0.000 description 8
238000000746 purification Methods 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000011734 sodium Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000000052 vinegar Substances 0.000 description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
241000700159 Rattus Species 0.000 description 7
239000012043 crude product Substances 0.000 description 7
229930195733 hydrocarbon Natural products 0.000 description 7
150000002513 isocyanates Chemical class 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
229910000085 borane Inorganic materials 0.000 description 6
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
229940125396 insulin Drugs 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
108020004999 messenger RNA Proteins 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
208000024891 symptom Diseases 0.000 description 6
150000003626 triacylglycerols Chemical class 0.000 description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
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JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
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XJVIPPHGDPEDJL-UHFFFAOYSA-N thiourea;hydrochloride Chemical compound Cl.NC(N)=S XJVIPPHGDPEDJL-UHFFFAOYSA-N 0.000 description 1
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238000005533 tritiation Methods 0.000 description 1
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Classifications

- 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
- C07C275/28—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 carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—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 carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—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 carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- 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
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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
- C07C275/28—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 carbon atoms of six-membered aromatic rings of a carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
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General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Obesity (AREA)
Cardiology (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Epidemiology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

TW092129192A 2002-10-21 2003-10-21 Substituted tetralins and indanes TW200418773A (en)

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US41993502P	2002-10-21	2002-10-21
US49527003P	2003-08-15	2003-08-15

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EP (1)	EP1569897A1 (pl)
JP (1)	JP2006503916A (pl)
KR (1)	KR20050055773A (pl)
AU (1)	AU2003277441B2 (pl)
BR (1)	BR0315596A (pl)
CA (1)	CA2502661A1 (pl)
CR (1)	CR7795A (pl)
EA (1)	EA009553B1 (pl)
EG (1)	EG24842A (pl)
HR (1)	HRP20050335A2 (pl)
MX (1)	MXPA05004191A (pl)
NO (1)	NO20052199L (pl)
NZ (1)	NZ539510A (pl)
PL (1)	PL376325A1 (pl)
RS (1)	RS20050318A (pl)
TW (1)	TW200418773A (pl)
WO (1)	WO2004037778A1 (pl)

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Publication number	Priority date	Publication date	Assignee	Title
AU2003279996B2 (en) *	2002-10-21	2009-07-09	Janssen Pharmaceutica, N.V.	Substituted tetralins and indanes and their use
CA2503405A1 (en) *	2002-10-21	2004-05-06	Janssen Pharmaceutica, N.V.	Treating syndrome x with substituted tetralins and indanes
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WO2006049941A2 (en) *	2004-10-27	2006-05-11	Neurogen Corporation	Diaryl ureas as cb1 antagonists
BRPI0620468A2 (pt)	2005-12-22	2011-11-08	Transtech Pharma, Inc.	ácidos fenóxi acéticos como ativadores de ppar delta

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2003
- 2003-10-17 KR KR1020057006795A patent/KR20050055773A/ko not_active Withdrawn
- 2003-10-17 EA EA200500515A patent/EA009553B1/ru not_active IP Right Cessation
- 2003-10-17 RS YUP-2005/0318A patent/RS20050318A/sr unknown
- 2003-10-17 HR HR20050335A patent/HRP20050335A2/hr not_active Application Discontinuation
- 2003-10-17 NZ NZ539510A patent/NZ539510A/en not_active IP Right Cessation
- 2003-10-17 PL PL03376325A patent/PL376325A1/pl not_active Application Discontinuation
- 2003-10-17 AU AU2003277441A patent/AU2003277441B2/en not_active Ceased
- 2003-10-17 CA CA002502661A patent/CA2502661A1/en not_active Withdrawn
- 2003-10-17 WO PCT/US2003/033090 patent/WO2004037778A1/en not_active Ceased
- 2003-10-17 EP EP03809577A patent/EP1569897A1/en not_active Withdrawn
- 2003-10-17 JP JP2005501629A patent/JP2006503916A/ja not_active Withdrawn
- 2003-10-17 BR BR0315596-0A patent/BR0315596A/pt not_active IP Right Cessation
- 2003-10-17 MX MXPA05004191A patent/MXPA05004191A/es active IP Right Grant
- 2003-10-21 TW TW092129192A patent/TW200418773A/zh unknown
2005
- 2005-04-18 CR CR7795A patent/CR7795A/es not_active Application Discontinuation
- 2005-04-20 EG EGNA2005000152 patent/EG24842A/xx active
- 2005-05-04 NO NO20052199A patent/NO20052199L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
MXPA05004191A (es)	2006-01-27
RS20050318A (sr)	2007-09-21
PL376325A1 (pl)	2005-12-27
CR7795A (es)	2012-10-25
EP1569897A1 (en)	2005-09-07
BR0315596A (pt)	2005-09-06
EA009553B1 (ru)	2008-02-28
HRP20050335A2 (en)	2006-05-31
AU2003277441A1 (en)	2004-05-13
EA200500515A1 (ru)	2005-10-27
NZ539510A (en)	2008-01-31
JP2006503916A (ja)	2006-02-02
CA2502661A1 (en)	2004-05-06
WO2004037778A1 (en)	2004-05-06
KR20050055773A (ko)	2005-06-13
AU2003277441B2 (en)	2009-05-07
EG24842A (en)	2010-10-13
NO20052199L (no)	2005-06-24

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