AU2002253010B8 - Acylated indanyl amines and their use as pharmaceuticals - Google Patents
Acylated indanyl amines and their use as pharmaceuticals Download PDFInfo
- Publication number
- AU2002253010B8 AU2002253010B8 AU2002253010A AU2002253010A AU2002253010B8 AU 2002253010 B8 AU2002253010 B8 AU 2002253010B8 AU 2002253010 A AU2002253010 A AU 2002253010A AU 2002253010 A AU2002253010 A AU 2002253010A AU 2002253010 B8 AU2002253010 B8 AU 2002253010B8
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- phenyl
- group
- indan
- heteroaryl
- 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.)
- Ceased
Links
- -1 Acylated indanyl amines Chemical class 0.000 title claims description 380
- 239000003814 drug Substances 0.000 title claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 198
- 229910052736 halogen Inorganic materials 0.000 claims description 134
- 150000002367 halogens Chemical class 0.000 claims description 130
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 125
- 150000001875 compounds Chemical class 0.000 claims description 121
- 125000001072 heteroaryl group Chemical group 0.000 claims description 119
- 125000002577 pseudohalo group Chemical group 0.000 claims description 94
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 51
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- LMHHFZAXSANGGM-UHFFFAOYSA-N 2-aminoindane Chemical compound C1=CC=C2CC(N)CC2=C1 LMHHFZAXSANGGM-UHFFFAOYSA-N 0.000 claims description 36
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 36
- 125000005842 heteroatom Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 23
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 23
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000000243 solution Substances 0.000 claims description 21
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 20
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 14
- 229910052796 boron Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 230000014509 gene expression Effects 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 201000001320 Atherosclerosis Diseases 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 230000003511 endothelial effect Effects 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 210000001367 artery Anatomy 0.000 claims description 8
- 208000029078 coronary artery disease Diseases 0.000 claims description 8
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 7
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 7
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 208000002249 Diabetes Complications Diseases 0.000 claims description 6
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 6
- 206010019280 Heart failures Diseases 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 208000007718 Stable Angina Diseases 0.000 claims description 6
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 6
- 230000008694 endothelial dysfunction Effects 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 230000002093 peripheral effect Effects 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims description 5
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 5
- 208000007536 Thrombosis Diseases 0.000 claims description 5
- 208000007814 Unstable Angina Diseases 0.000 claims description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 208000037803 restenosis Diseases 0.000 claims description 5
- 239000003826 tablet Substances 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
- 208000007530 Essential hypertension Diseases 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 206010018367 Glomerulonephritis chronic Diseases 0.000 claims description 4
- 208000001132 Osteoporosis Diseases 0.000 claims description 4
- 201000001068 Prinzmetal angina Diseases 0.000 claims description 4
- 201000003099 Renovascular Hypertension Diseases 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- 201000004239 Secondary hypertension Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 208000009325 Variant Angina Pectoris Diseases 0.000 claims description 4
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 4
- 230000033115 angiogenesis Effects 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 208000020832 chronic kidney disease Diseases 0.000 claims description 4
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims description 4
- 230000007882 cirrhosis Effects 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 239000007903 gelatin capsule Substances 0.000 claims description 4
- 201000001881 impotence Diseases 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 208000017169 kidney disease Diseases 0.000 claims description 4
- 210000004185 liver Anatomy 0.000 claims description 4
- KJRZWIKUHMWWFM-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-4-methylsulfanylbenzamide Chemical compound C1=CC(SC)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 KJRZWIKUHMWWFM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 230000002861 ventricular Effects 0.000 claims description 4
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
- IGQDZYVWSOKCCO-UHFFFAOYSA-N 2-chloro-n-(2,3-dihydro-1h-inden-2-yl)-6-methylpyridine-3-carboxamide Chemical compound ClC1=NC(C)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 IGQDZYVWSOKCCO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
- LEKWXWJZSOPFII-UHFFFAOYSA-N 4-bromo-2-chloro-n-(2,3-dihydro-1h-inden-2-yl)benzamide Chemical compound ClC1=CC(Br)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 LEKWXWJZSOPFII-UHFFFAOYSA-N 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- NQSTXRNSHFJLMH-UHFFFAOYSA-N 5-acetyl-n-(2,3-dihydro-1h-inden-2-yl)thiophene-2-carboxamide Chemical compound S1C(C(=O)C)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 NQSTXRNSHFJLMH-UHFFFAOYSA-N 0.000 claims description 3
- 239000008298 dragée Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 239000007943 implant Substances 0.000 claims description 3
- 238000001802 infusion Methods 0.000 claims description 3
- 230000007334 memory performance Effects 0.000 claims description 3
- 239000003094 microcapsule Substances 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- MPXUHFXUIZRORK-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-4-ethylsulfanylbenzamide Chemical compound C1=CC(SCC)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 MPXUHFXUIZRORK-UHFFFAOYSA-N 0.000 claims description 3
- OHHGMOCQFHFWPD-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)thiophene-2-carboxamide Chemical compound C1C2=CC=CC=C2CC1NC(=O)C1=CC=CS1 OHHGMOCQFHFWPD-UHFFFAOYSA-N 0.000 claims description 3
- 239000007922 nasal spray Substances 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 239000006187 pill Substances 0.000 claims description 3
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 3
- 239000007940 sugar coated tablet Substances 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
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- 239000006188 syrup Substances 0.000 claims description 3
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- GHTDODSYDCPOCW-UHFFFAOYSA-N 1h-indole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2C=CNC2=C1 GHTDODSYDCPOCW-UHFFFAOYSA-N 0.000 claims description 2
- KRHMOVIJQRSYJV-UHFFFAOYSA-N 2-bromo-4-chloro-n-(2,3-dihydro-1h-inden-2-yl)benzamide Chemical compound BrC1=CC(Cl)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 KRHMOVIJQRSYJV-UHFFFAOYSA-N 0.000 claims description 2
- LFUYUFFYKMDILR-UHFFFAOYSA-N 2-chloro-n-(2,3-dihydro-1h-inden-2-yl)benzamide Chemical compound ClC1=CC=CC=C1C(=O)NC1CC2=CC=CC=C2C1 LFUYUFFYKMDILR-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- YSRBFWINKVMWLT-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-hydroxy-4-methylbenzamide Chemical compound OC1=CC(C)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 YSRBFWINKVMWLT-UHFFFAOYSA-N 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- OKCJNSDIVCXYAL-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2,2-difluoro-1,3-benzodioxole-5-carboxamide Chemical compound C1C2=CC=CC=C2CC1NC(=O)C1=CC=C2OC(F)(F)OC2=C1 OKCJNSDIVCXYAL-UHFFFAOYSA-N 0.000 claims 3
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 2
- XXOKIKKIMRAIDZ-UHFFFAOYSA-N 2-amino-n-(2,3-dihydro-1h-inden-2-yl)benzamide Chemical compound NC1=CC=CC=C1C(=O)NC1CC2=CC=CC=C2C1 XXOKIKKIMRAIDZ-UHFFFAOYSA-N 0.000 claims 2
- KLMRGIURJNYXHB-UHFFFAOYSA-N 3-chloro-n-(2,3-dihydro-1h-inden-2-yl)-4-methylthiophene-2-carboxamide Chemical compound CC1=CSC(C(=O)NC2CC3=CC=CC=C3C2)=C1Cl KLMRGIURJNYXHB-UHFFFAOYSA-N 0.000 claims 2
- WYRYWQXPSLVYJO-UHFFFAOYSA-N 3-chloro-n-(2,3-dihydro-1h-inden-2-yl)-4-propan-2-ylsulfonylthiophene-2-carboxamide Chemical compound CC(C)S(=O)(=O)C1=CSC(C(=O)NC2CC3=CC=CC=C3C2)=C1Cl WYRYWQXPSLVYJO-UHFFFAOYSA-N 0.000 claims 2
- QRENWBKXNZJPCB-UHFFFAOYSA-N 5-bromo-n-(2,3-dihydro-1h-inden-2-yl)thiophene-2-carboxamide Chemical compound S1C(Br)=CC=C1C(=O)NC1CC2=CC=CC=C2C1 QRENWBKXNZJPCB-UHFFFAOYSA-N 0.000 claims 2
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- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
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- KPVOHHOWYRESDB-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2,5-dimethyl-1h-pyrrole-3-carboxamide Chemical compound N1C(C)=CC(C(=O)NC2CC3=CC=CC=C3C2)=C1C KPVOHHOWYRESDB-UHFFFAOYSA-N 0.000 claims 2
- NIHUGSQILVAFLW-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-3-methylthiophene-2-carboxamide Chemical compound C1=CSC(C(=O)NC2CC3=CC=CC=C3C2)=C1C NIHUGSQILVAFLW-UHFFFAOYSA-N 0.000 claims 2
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- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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Classifications
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01102850 | 2001-02-13 | ||
| EP01102850.3 | 2001-02-13 | ||
| PCT/EP2002/001444 WO2002064545A1 (en) | 2001-02-13 | 2002-02-12 | Acylated indanyl amines and their use as pharmaceuticals |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| AU2002253010A1 AU2002253010A1 (en) | 2003-02-20 |
| AU2002253010B2 AU2002253010B2 (en) | 2008-02-28 |
| AU2002253010B9 AU2002253010B9 (en) | 2008-07-31 |
| AU2002253010B8 true AU2002253010B8 (en) | 2009-04-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002253010A Ceased AU2002253010B8 (en) | 2001-02-13 | 2002-02-12 | Acylated indanyl amines and their use as pharmaceuticals |
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