OA10980A - Substituted 6,6-hetero-bicyclic derivatives - Google Patents

Substituted 6,6-hetero-bicyclic derivatives Download PDF

Info

Publication number: OA10980A
Authority: OA; OAPI
Prior art keywords: alkyl; compound according; methyl; phenyl; aikyl
Prior art date: 1996-08-27

Application number

OA9900039A

Other languages

English (en)

Inventor

Yuhpyng Liang Chen

Original Assignee

Pfizer

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.)

1996-08-27

Filing date

1999-02-25

Publication date

2001-11-02

1999-02-25 Application filed by Pfizer filed Critical Pfizer

2001-11-02 Publication of OA10980A publication Critical patent/OA10980A/en

Links

150000001875 compounds Chemical class 0.000 claims abstract description 223
102100021752 Corticoliberin Human genes 0.000 claims abstract description 20
229940088597 hormone Drugs 0.000 claims abstract description 7
239000005556 hormone Substances 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims description 155
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 65
-1 hydroxy, fluoro, chloro, bromo, iodo Chemical group 0.000 claims description 55
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
125000001309 chloro group Chemical group Cl* 0.000 claims description 30
125000002947 alkylene group Chemical group 0.000 claims description 29
229910052799 carbon Inorganic materials 0.000 claims description 29
238000000034 method Methods 0.000 claims description 28
229910052760 oxygen Inorganic materials 0.000 claims description 26
125000001246 bromo group Chemical group Br* 0.000 claims description 24
125000001153 fluoro group Chemical group F* 0.000 claims description 24
125000002346 iodo group Chemical group I* 0.000 claims description 24
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
208000035475 disorder Diseases 0.000 claims description 22
125000001424 substituent group Chemical group 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 16
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
229910052684 Cerium Inorganic materials 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 12
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
239000011593 sulfur Chemical group 0.000 claims description 10
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125000003545 alkoxy group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
229940079593 drug Drugs 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000006413 ring segment Chemical group 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
108091008324 binding proteins Proteins 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
230000002401 inhibitory effect Effects 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
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125000005605 benzo group Chemical group 0.000 claims description 6
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125000004076 pyridyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 4
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125000004429 atom Chemical group 0.000 claims description 4
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ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 4
229960002069 diamorphine Drugs 0.000 claims description 4
230000002600 fibrillogenic effect Effects 0.000 claims description 4
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208000026278 immune system disease Diseases 0.000 claims description 4
208000028867 ischemia Diseases 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
230000004770 neurodegeneration Effects 0.000 claims description 4
208000015122 neurodegenerative disease Diseases 0.000 claims description 4
230000001314 paroxysmal effect Effects 0.000 claims description 4
208000019899 phobic disease Diseases 0.000 claims description 4
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210000000278 spinal cord Anatomy 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
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241000283690 Bos taurus Species 0.000 claims description 3
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208000005314 Multi-Infarct Dementia Diseases 0.000 claims description 3
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208000026725 cyclothymic disease Diseases 0.000 claims description 3
230000003993 interaction Effects 0.000 claims description 3
201000008482 osteoarthritis Diseases 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
102000004169 proteins and genes Human genes 0.000 claims description 3
108090000623 proteins and genes Proteins 0.000 claims description 3
206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
208000019116 sleep disease Diseases 0.000 claims description 3
208000024891 symptom Diseases 0.000 claims description 3
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical class N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 2
SQVZUGHPSMFDBH-UHFFFAOYSA-N 2-methyl-4-pentan-3-yloxy-8-(2,4,6-trimethylphenyl)quinoline Chemical compound C1=CC=C2C(OC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C SQVZUGHPSMFDBH-UHFFFAOYSA-N 0.000 claims description 2
BHHMPZQRVWVAAR-UHFFFAOYSA-N 7-bromo-8-methylpyrido[2,3-b]pyrazine Chemical compound C1=CN=C2C(C)=C(Br)C=NC2=N1 BHHMPZQRVWVAAR-UHFFFAOYSA-N 0.000 claims description 2
OCPRQWREMAXTOZ-UHFFFAOYSA-N 7-methyl-5-pentan-3-yloxy-1-(2,4,6-trimethylphenyl)-2h-pyrido[2,3-d][1,3]oxazin-4-one Chemical compound C1OC(=O)C=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C OCPRQWREMAXTOZ-UHFFFAOYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
208000034189 Sclerosis Diseases 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
229960003920 cocaine Drugs 0.000 claims description 2
206010061428 decreased appetite Diseases 0.000 claims description 2
230000004064 dysfunction Effects 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
101150009274 nhr-1 gene Proteins 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
125000005493 quinolyl group Chemical group 0.000 claims description 2
125000006850 spacer group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
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 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
102000014914 Carrier Proteins Human genes 0.000 claims 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
206010015037 epilepsy Diseases 0.000 claims 2
ZFRUGZMCGCYBRC-UHFFFAOYSA-N 1h-1,8-naphthyridin-2-one Chemical compound C1=CC=NC2=NC(O)=CC=C21 ZFRUGZMCGCYBRC-UHFFFAOYSA-N 0.000 claims 1
URJKRCBBKTXOHS-UHFFFAOYSA-O 2-(2-hydroxy-phenyl)-3h-benzoimidazole-5-carboxamidine Chemical group N1C2=CC(C(=[NH2+])N)=CC=C2N=C1C1=CC=CC=C1O URJKRCBBKTXOHS-UHFFFAOYSA-O 0.000 claims 1
OBYABPUZVBFQAU-UHFFFAOYSA-N 2-methyl-n-pentan-3-yl-8-(2,4,6-trimethylphenyl)quinolin-4-amine Chemical compound C1=CC=C2C(NC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C OBYABPUZVBFQAU-UHFFFAOYSA-N 0.000 claims 1
LAQJGAKLLZAETL-UHFFFAOYSA-N 2h-pyrazin-3-one Chemical compound O=C1CN=CC=N1 LAQJGAKLLZAETL-UHFFFAOYSA-N 0.000 claims 1
PUZLSXWSLTZXSJ-UHFFFAOYSA-N 4-[butyl(ethyl)amino]-2,6-dimethyl-8-(2,4,6-trimethylphenyl)-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(C)CC=2C(N(CC)CCCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C PUZLSXWSLTZXSJ-UHFFFAOYSA-N 0.000 claims 1
UEJHCIZKAAFBCH-UHFFFAOYSA-N 4-chloro-7-methyl-5-pentan-3-yloxy-1-(2,4,6-trimethylphenyl)pyrido[2,3-d]pyrimidin-2-one Chemical compound O=C1N=C(Cl)C=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C UEJHCIZKAAFBCH-UHFFFAOYSA-N 0.000 claims 1
IPPBHNMFESFVGT-UHFFFAOYSA-N 6-methyl-8-pentan-3-yloxy-4-(2,4,6-trimethylphenyl)-2,3-dihydro-1h-pyrido[2,3-b]pyrazine Chemical compound C1CNC=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C IPPBHNMFESFVGT-UHFFFAOYSA-N 0.000 claims 1
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
238000005481 NMR spectroscopy Methods 0.000 description 28
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238000006243 chemical reaction Methods 0.000 description 18
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239000007787 solid Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
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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 10
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
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238000004440 column chromatography Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000000499 gel Substances 0.000 description 6
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
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230000003042 antagnostic effect Effects 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
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239000007900 aqueous suspension Substances 0.000 description 1
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RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
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WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
150000005347 biaryls Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000006664 bond formation reaction Methods 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
MAPRDOKILZKGDP-UHFFFAOYSA-N bromo-chloro-iodomethanesulfonic acid Chemical group OS(=O)(=O)C(Cl)(Br)I MAPRDOKILZKGDP-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
238000004040 coloring Methods 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
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239000002769 corticotropin releasing factor antagonist Substances 0.000 description 1
108010083720 corticotropin releasing factor-binding protein Proteins 0.000 description 1
230000005595 deprotonation Effects 0.000 description 1
238000010537 deprotonation reaction Methods 0.000 description 1
HMOJUCUJIXEKOH-UHFFFAOYSA-N dicyanoalumanylformonitrile Chemical compound N#C[Al](C#N)C#N HMOJUCUJIXEKOH-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
239000012039 electrophile Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
LKHZKAFQINWNAH-UHFFFAOYSA-N ethyl 3-[4-chloro-2-methyl-6-(2,4,6-trimethylanilino)pyrimidin-5-yl]-2-methylpropanoate Chemical compound CCOC(=O)C(C)CC1=C(Cl)N=C(C)N=C1NC1=C(C)C=C(C)C=C1C LKHZKAFQINWNAH-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000008629 immune suppression Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
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238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
230000036651 mood Effects 0.000 description 1
QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
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239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000003488 releasing hormone Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
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239000006188 syrup Substances 0.000 description 1
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239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
230000009385 viral infection Effects 0.000 description 1

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
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- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/42—Drugs for disorders of the endocrine system of the suprarenal hormones for decreasing, blocking or antagonising the activity of mineralocorticosteroids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—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
- 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
- C07D215/18—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—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
- 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
- C07D215/42—Nitrogen atoms attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4

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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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OA9900039A 1996-08-27 1999-02-25 Substituted 6,6-hetero-bicyclic derivatives OA10980A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US2465996P	1996-08-27	1996-08-27

Publications (1)

Publication Number	Publication Date
OA10980A true OA10980A (en)	2001-11-02

Family

ID=21821740

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900039A OA10980A (en)	1996-08-27	1999-02-25	Substituted 6,6-hetero-bicyclic derivatives

Country Status (40)

Country	Link
EP (1)	EP0925298B1 (fr)
JP (1)	JP2000502722A (fr)
KR (1)	KR100457759B1 (fr)
CN (2)	CN1191236C (fr)
AP (1)	AP1164A (fr)
AR (2)	AR009321A1 (fr)
AT (1)	ATE264327T1 (fr)
AU (1)	AU726771C (fr)
BG (1)	BG64316B1 (fr)
BR (1)	BR9711262A (fr)
CA (1)	CA2263913C (fr)
CO (1)	CO4930259A1 (fr)
CZ (1)	CZ67799A3 (fr)
DE (1)	DE69728676T2 (fr)
DK (1)	DK0925298T3 (fr)
DZ (1)	DZ2299A1 (fr)
EA (1)	EA002607B1 (fr)
ES (1)	ES2216157T3 (fr)
GT (1)	GT199700093A (fr)
HR (1)	HRP970452A2 (fr)
ID (1)	ID18189A (fr)
IL (1)	IL128049A (fr)
IS (1)	IS4970A (fr)
MY (1)	MY132671A (fr)
NO (1)	NO316273B1 (fr)
NZ (1)	NZ333728A (fr)
OA (1)	OA10980A (fr)
PA (1)	PA8435001A1 (fr)
PE (1)	PE108698A1 (fr)
PL (1)	PL331988A1 (fr)
PT (1)	PT925298E (fr)
SI (1)	SI0925298T1 (fr)
SK (1)	SK22599A3 (fr)
TN (1)	TNSN97144A1 (fr)
TR (1)	TR199900408T2 (fr)
TW (1)	TW477787B (fr)
UA (1)	UA66345C2 (fr)
WO (1)	WO1998008846A1 (fr)
YU (1)	YU35697A (fr)
ZA (1)	ZA977652B (fr)

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1997
- 1997-07-15 TW TW086109990A patent/TW477787B/zh not_active IP Right Cessation
- 1997-07-21 AU AU33557/97A patent/AU726771C/en not_active Ceased
- 1997-07-21 PL PL97331988A patent/PL331988A1/xx unknown
- 1997-07-21 DK DK97929464T patent/DK0925298T3/da active
- 1997-07-21 SK SK225-99A patent/SK22599A3/sk unknown
- 1997-07-21 CN CNB021020574A patent/CN1191236C/zh not_active Expired - Fee Related
- 1997-07-21 DE DE69728676T patent/DE69728676T2/de not_active Expired - Fee Related
- 1997-07-21 ES ES97929464T patent/ES2216157T3/es not_active Expired - Lifetime
- 1997-07-21 UA UA99020647A patent/UA66345C2/uk unknown
- 1997-07-21 PT PT97929464T patent/PT925298E/pt unknown
- 1997-07-21 CZ CZ99677A patent/CZ67799A3/cs unknown
- 1997-07-21 CA CA002263913A patent/CA2263913C/fr not_active Expired - Fee Related
- 1997-07-21 CN CNB971973555A patent/CN1138774C/zh not_active Expired - Fee Related
- 1997-07-21 IL IL12804997A patent/IL128049A/en not_active IP Right Cessation
- 1997-07-21 NZ NZ333728A patent/NZ333728A/xx unknown
- 1997-07-21 WO PCT/IB1997/000904 patent/WO1998008846A1/fr not_active Ceased
- 1997-07-21 TR TR1999/00408T patent/TR199900408T2/xx unknown
- 1997-07-21 KR KR10-1999-7001619A patent/KR100457759B1/ko not_active Expired - Fee Related
- 1997-07-21 EA EA199900166A patent/EA002607B1/ru not_active IP Right Cessation
- 1997-07-21 JP JP10511427A patent/JP2000502722A/ja active Pending
- 1997-07-21 SI SI9730642T patent/SI0925298T1/xx unknown
- 1997-07-21 BR BR9711262A patent/BR9711262A/pt not_active Application Discontinuation
- 1997-07-21 EP EP97929464A patent/EP0925298B1/fr not_active Expired - Lifetime
- 1997-07-21 AT AT97929464T patent/ATE264327T1/de not_active IP Right Cessation
- 1997-07-30 PA PA19978435001A patent/PA8435001A1/es unknown
- 1997-08-13 GT GT199700093A patent/GT199700093A/es unknown
- 1997-08-21 AP APAP/P/1997/001076A patent/AP1164A/en active
- 1997-08-22 PE PE1997000751A patent/PE108698A1/es not_active Application Discontinuation
- 1997-08-22 HR HR60/024,659A patent/HRP970452A2/hr not_active Application Discontinuation
- 1997-08-25 AR ARP970103851A patent/AR009321A1/es not_active Application Discontinuation
- 1997-08-25 ID IDP972952A patent/ID18189A/id unknown
- 1997-08-26 MY MYPI97003918A patent/MY132671A/en unknown
- 1997-08-26 YU YU35697A patent/YU35697A/sr unknown
- 1997-08-26 CO CO97049282A patent/CO4930259A1/es unknown
- 1997-08-26 ZA ZA977652A patent/ZA977652B/xx unknown
- 1997-08-26 DZ DZ970149A patent/DZ2299A1/fr active
- 1997-08-26 TN TNTNSN97144A patent/TNSN97144A1/fr unknown
1999
- 1999-02-05 IS IS4970A patent/IS4970A/is unknown
- 1999-02-22 BG BG103192A patent/BG64316B1/bg unknown
- 1999-02-25 NO NO19990892A patent/NO316273B1/no not_active IP Right Cessation
- 1999-02-25 OA OA9900039A patent/OA10980A/en unknown
2001
- 2001-01-10 AR ARP010100097A patent/AR026826A1/es unknown

Also Published As

Publication number	Publication date
JP2000502722A (ja)	2000-03-07
DK0925298T3 (da)	2004-08-09
KR100457759B1 (ko)	2004-11-18
PE108698A1 (es)	1999-01-23
HRP970452A2 (en)	1998-08-31
PL331988A1 (en)	1999-08-16
CO4930259A1 (es)	2000-06-27
GT199700093A (es)	1999-02-04
ID18189A (id)	1998-03-12
IS4970A (is)	1999-02-05
NO316273B1 (no)	2004-01-05
DE69728676T2 (de)	2004-09-30
IL128049A (en)	2004-12-15
NO990892D0 (no)	1999-02-25
EA199900166A1 (ru)	1999-08-26
CN1138774C (zh)	2004-02-18
EA002607B1 (ru)	2002-06-27
BG64316B1 (bg)	2004-09-30
AU726771B2 (en)	2000-11-23
AP9701076A0 (en)	1997-10-31
AR026826A1 (es)	2003-02-26
TR199900408T2 (xx)	1999-05-21
NZ333728A (en)	2000-11-24
EP0925298A1 (fr)	1999-06-30
PT925298E (pt)	2004-07-30
CN1191236C (zh)	2005-03-02
IL128049A0 (en)	1999-11-30
ATE264327T1 (de)	2004-04-15
NO990892L (no)	1999-02-25
AU3355797A (en)	1998-03-19
TNSN97144A1 (fr)	2005-03-15
CA2263913A1 (fr)	1998-03-05
AU726771C (en)	2004-11-11
WO1998008846A1 (fr)	1998-03-05
ES2216157T3 (es)	2004-10-16
PA8435001A1 (es)	2002-07-30
CA2263913C (fr)	2004-06-29
YU35697A (en)	1999-11-22
SI0925298T1 (en)	2004-08-31
BR9711262A (pt)	1999-08-17
HK1019597A1 (en)	2000-02-18
CN1367169A (zh)	2002-09-04
DZ2299A1 (fr)	2002-12-25
CN1228091A (zh)	1999-09-08
TW477787B (en)	2002-03-01
CZ67799A3 (cs)	1999-11-17
EP0925298B1 (fr)	2004-04-14
DE69728676D1 (de)	2004-05-19
AR009321A1 (es)	2000-04-12
MY132671A (en)	2007-10-31
AP1164A (en)	2003-06-30
BG103192A (en)	1999-09-30
UA66345C2 (en)	2004-05-17
SK22599A3 (en)	2000-07-11
KR20000035898A (ko)	2000-06-26
ZA977652B (en)	1999-02-26

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