PH26783A - 7-aryl and heteroaryl ethers of desacetylforskolin - Google Patents

7-aryl and heteroaryl ethers of desacetylforskolin Download PDF

Info

Publication number: PH26783A
Authority: PH; Philippines
Prior art keywords: formula; group; loweralkyl; compound according; hvdrogen
Prior art date: 1989-01-11

Application number

PH39863A

Other languages

English (en)

Inventor

Walter Raymond Kosley Jr

Bettina Spahl

Gerard J Onmalley

Original Assignee

Hoechst Roussel Pharma

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.)

1989-01-11

Filing date

1990-01-09

Publication date

1992-10-13

1990-01-09 Application filed by Hoechst Roussel Pharma filed Critical Hoechst Roussel Pharma

1992-10-13 Publication of PH26783A publication Critical patent/PH26783A/en

Links

-1 heteroaryl ethers Chemical class 0.000 title claims description 38
WPDITXOBNLYZHH-KAACEJSMSA-N (3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-5,6,10,10b-tetrahydroxy-3,4a,7,7,10a-pentamethyl-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-1-one Chemical compound O1[C@@](C)(C=C)CC(=O)[C@]2(O)[C@@]3(C)[C@@H](O)CCC(C)(C)[C@@H]3[C@H](O)[C@H](O)[C@]21C WPDITXOBNLYZHH-KAACEJSMSA-N 0.000 title description 7
WPDITXOBNLYZHH-UHFFFAOYSA-N desacetylforskolin Natural products O1C(C)(C=C)CC(=O)C2(O)C3(C)C(O)CCC(C)(C)C3C(O)C(O)C21C WPDITXOBNLYZHH-UHFFFAOYSA-N 0.000 title description 7
OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 claims description 119
235000013350 formula milk Nutrition 0.000 claims description 78
229910052739 hydrogen Inorganic materials 0.000 claims description 65
150000001875 compounds Chemical class 0.000 claims description 64
SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 claims description 61
OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 claims description 61
229910052757 nitrogen Inorganic materials 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 34
150000002431 hydrogen Chemical class 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
230000003287 optical effect Effects 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
230000000747 cardiac effect Effects 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 3
101100194627 Caenorhabditis elegans rgs-1 gene Proteins 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 2
206010019280 Heart failures Diseases 0.000 claims 1
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims 1
239000002671 adjuvant Substances 0.000 claims 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
239000002361 compost Substances 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 78
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 38
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
229910052799 carbon Inorganic materials 0.000 description 29
150000001241 acetals Chemical class 0.000 description 28
239000000243 solution Substances 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
238000002360 preparation method Methods 0.000 description 22
239000000499 gel Substances 0.000 description 19
239000000463 material Substances 0.000 description 18
239000000203 mixture Substances 0.000 description 17
238000004458 analytical method Methods 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 14
238000001819 mass spectrum Methods 0.000 description 14
241000206607 Porphyra umbilicalis Species 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
150000004160 forskolin derivatives Chemical class 0.000 description 11
239000000047 product Substances 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000000725 suspension Substances 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
229940073584 methylene chloride Drugs 0.000 description 8
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
239000002253 acid Substances 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
239000011591 potassium Substances 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
239000000284 extract Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
ATHHXGZTWNVVOU-UHFFFAOYSA-N monomethyl-formamide Natural products CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 5
238000006254 arylation reaction Methods 0.000 description 4
210000002837 heart atrium Anatomy 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 3
UTBGRJQUEBNKAL-UHFFFAOYSA-N 6-chloro-1-methylpurine Chemical compound CN1C=NC2=NC=NC2=C1Cl UTBGRJQUEBNKAL-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 3
102100025734 Dual specificity protein phosphatase CDC14A Human genes 0.000 description 3
101000932600 Homo sapiens Dual specificity protein phosphatase CDC14A Proteins 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000004703 alkoxides Chemical class 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003814 drug Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000010410 layer Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 3
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 3
239000007858 starting material Substances 0.000 description 3
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000005418 aryl aryl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
239000002585 base Substances 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
229940125904 compound 1 Drugs 0.000 description 2
238000001212 derivatisation Methods 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
IUIWALGJZIUPKV-UHFFFAOYSA-M trimethyl-[2-[4-oxo-4-[2-(trimethylazaniumyl)ethoxy]butanoyl]oxyethyl]azanium;chloride Chemical group [Cl-].C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C IUIWALGJZIUPKV-UHFFFAOYSA-M 0.000 description 2
229910052720 vanadium Inorganic materials 0.000 description 2
LOTKRQAVGJMPNV-UHFFFAOYSA-N 1-fluoro-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C([N+]([O-])=O)=C1 LOTKRQAVGJMPNV-UHFFFAOYSA-N 0.000 description 1
OGVLEPMNNPZAPS-UHFFFAOYSA-N 2,3-difluoropyridine Chemical compound FC1=CC=CN=C1F OGVLEPMNNPZAPS-UHFFFAOYSA-N 0.000 description 1
MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
101100055634 Arabidopsis thaliana ANT gene Proteins 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
108700018454 CDC15 Proteins 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
235000021508 Coleus Nutrition 0.000 description 1
244000061182 Coleus blumei Species 0.000 description 1
241000518994 Conta Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
101150096418 Mepe gene Proteins 0.000 description 1
241000169439 Nocar Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000282887 Suidae Species 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
101150008083 ant gene Proteins 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000008378 aryl ethers Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001723 carbon free-radicals Chemical class 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
101150081467 cdc15 gene Proteins 0.000 description 1
GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 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
239000011521 glass Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
150000001761 labdane diterpenoid derivatives Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000005246 left atrium Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 description 1
239000000346 nonvolatile oil Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

PH39863A 1989-01-11 1990-01-09 7-aryl and heteroaryl ethers of desacetylforskolin PH26783A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/295,840 US4999351A (en)	1989-01-11	1989-01-11	7-aryl and heteroaryl ethers of desacetylforskolin

Publications (1)

Publication Number	Publication Date
PH26783A true PH26783A (en)	1992-10-13

Family

ID=23139429

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH39863A PH26783A (en)	1989-01-11	1990-01-09	7-aryl and heteroaryl ethers of desacetylforskolin

Country Status (13)

Country	Link
US (1)	US4999351A (no)
EP (1)	EP0378159A1 (no)
JP (1)	JPH02221271A (no)
AU (1)	AU621448B2 (no)
CA (1)	CA2007513A1 (no)
FI (1)	FI900102A (no)
HU (1)	HUT53631A (no)
IL (1)	IL93019A0 (no)
NO (1)	NO900119L (no)
NZ (1)	NZ232057A (no)
PH (1)	PH26783A (no)
PT (1)	PT92823A (no)
ZA (1)	ZA90167B (no)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5177207A (en) *	1989-01-11	1993-01-05	Hoechst-Roussel Pharmaceuticals, Inc.	7-aryl and heteroaryl ethers of desacetylforskolin
WO2002000240A2 (en)	2000-06-27	2002-01-03	Qualilife Pharmaceuticals Inc.	Compositions and methods for treating females sexual response

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2557784C2 (de) *	1975-12-22	1986-04-17	Hoechst Ag, 6230 Frankfurt	Forskolin, Verfahren zu dessen Gewinnung und diese Verbindung enthaltende pharmazeutische Präparate
DE2640275A1 (de) *	1976-09-08	1978-03-09	Hoechst Ag	Pharmakologisch wirksame substanz aus labiaten
DE2654796A1 (de) *	1976-12-03	1978-06-08	Hoechst Ag	Polyoxygenierte labdan-derivate
US4517200A (en) *	1982-12-27	1985-05-14	Schering-Plough Corporation	Method for treating allergic reactions with forskolin
US4564626A (en) *	1983-04-01	1986-01-14	Schering Corporation	Methods of inducing bronchodilation
DE3314999A1 (de) *	1983-04-26	1985-03-14	Behringwerke Ag, 3550 Marburg	Verwendung des diterpen-derivates forskolin zur immunstimulation
US4476140A (en) *	1983-05-16	1984-10-09	Yale University	Composition and method for treatment of glaucoma
DE3407514A1 (de) *	1984-03-01	1985-09-26	Hoechst Ag, 6230 Frankfurt	Verwendung von polyoxygenierten labdanderivaten zur behandlung von konstriktionen der atemwege
DE3502686A1 (de) *	1985-01-26	1986-08-14	Hoechst Ag, 6230 Frankfurt	Verfahren zur herstellung von labdan-derivaten und ihre verwendung als arzneimittel
US4666904A (en) *	1984-12-14	1987-05-19	Hoechst-Roussel Pharmaceuticals Inc.	Aminoacyllabdanes, pharmacuetical compositions and use
US4639446A (en) *	1984-12-14	1987-01-27	Hoechst-Roussel Pharmaceuticals Inc.	Aminoacyllabdanes, pharmaceutical compositions and use
DE3502685A1 (de) *	1985-01-26	1986-09-04	Hoechst Ag, 6230 Frankfurt	Forskolin, seine analoge und derivate, verfahren zu deren herstellung mittels mikrobieller umwandlungen und die anwendung dieser verbindungen als arzneimittel
US4672115A (en) *	1984-12-14	1987-06-09	Hoechst-Roussel Pharmaceuticals Inc.	Process for preparing aminoacyllabdanes
US4673752A (en) *	1984-12-14	1987-06-16	Hoechst-Roussel Pharmaceuticals Inc.	Aminoacyllabdanes
US4677103A (en) *	1985-03-01	1987-06-30	Hoechst-Roussel Pharmaceuticals Inc.	Labdane compounds, pharmaceutical compositions and use
US4639443A (en) *	1985-03-01	1987-01-27	Hoechst-Roussel Pharmaceuticals Inc.	Labdane compounds, pharmaceutical compositions and use
US4734513A (en) *	1986-03-31	1988-03-29	Hoechst-Roussel Pharmaceuticals Inc.	Method of synthesizing forskolin from 9-deoxyforskolin
US4740522A (en) *	1986-08-28	1988-04-26	Hoechst-Roussel Pharmaceuticals Inc.	Oxolabdanes useful as pharmaceuticals for reducing intraocular pressure
DE3730748A1 (de) *	1987-06-06	1988-12-22	Hoechst Ag	Neue polyoxygenierte labdanderivate, ein verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3887212T2 (de) *	1987-06-29	1994-06-01	Nippon Kayaku Kk	Verfahren zur Herstellung von Derivaten von 6,7-Diazyl-7-desacetylforskolin.
DE3737353A1 (de) *	1987-11-04	1989-05-18	Hoechst Ag	Neue acyllabdan-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als arzneimittel

1989
- 1989-01-11 US US07/295,840 patent/US4999351A/en not_active Expired - Lifetime
1990
- 1990-01-09 FI FI900102A patent/FI900102A/fi not_active IP Right Cessation
- 1990-01-09 EP EP90100341A patent/EP0378159A1/en not_active Withdrawn
- 1990-01-09 IL IL93019A patent/IL93019A0/xx unknown
- 1990-01-09 PH PH39863A patent/PH26783A/en unknown
- 1990-01-09 NZ NZ232057A patent/NZ232057A/xx unknown
- 1990-01-10 PT PT92823A patent/PT92823A/pt unknown
- 1990-01-10 ZA ZA90167A patent/ZA90167B/xx unknown
- 1990-01-10 CA CA002007513A patent/CA2007513A1/en not_active Abandoned
- 1990-01-10 HU HU9099A patent/HUT53631A/hu unknown
- 1990-01-10 NO NO90900119A patent/NO900119L/no unknown
- 1990-01-10 AU AU47837/90A patent/AU621448B2/en not_active Ceased
- 1990-01-10 JP JP2001647A patent/JPH02221271A/ja active Pending

Also Published As

Publication number	Publication date
HUT53631A (en)	1990-11-28
PT92823A (pt)	1990-07-31
FI900102A0 (fi)	1990-01-09
HU900099D0 (en)	1990-03-28
CA2007513A1 (en)	1990-07-11
AU621448B2 (en)	1992-03-12
IL93019A0 (en)	1990-11-05
US4999351A (en)	1991-03-12
NO900119L (no)	1990-07-12
NZ232057A (en)	1991-10-25
JPH02221271A (ja)	1990-09-04
ZA90167B (en)	1991-02-27
EP0378159A1 (en)	1990-07-18
FI900102A (fi)	1990-07-12
NO900119D0 (no)	1990-01-10
AU4783790A (en)	1990-07-19

Publication	Publication Date	Title
WO2020177653A1 (zh)	2020-09-10	吡嗪类衍生物及其在抑制shp2中的应用
US20230061083A1 (en)	2023-03-02	Kras g12c inhibitor compound and use thereof
AU753547B2 (en)	2002-10-24	Substituted tricyclics
US6350749B1 (en)	2002-02-26	Aminoguanidine hydrazone derivatives, process for producing the same and drugs thereof
CN109475530B (zh)	2022-03-01	用于治疗自身免疫性疾病的氨酰基吲唑免疫调节剂
JPH0649027A (ja)	1994-02-22	インドール誘導体
CZ30998A3 (cs)	1998-06-17	Farmaceutický prostředek obsahující deriváty 4-merkaptopyrrolidinu jako inhibitory farnesyl-transferázy
WO2021218939A1 (zh)	2021-11-04	稠环化合物及其在医药上的应用
KR20150032283A (ko)	2015-03-25	호흡기 합포체 바이러스의 항바이러스제로서의 헤테로사이클로 치환된 1,3-디하이드로-2h-벤즈이미다졸-2-온 유도체
WO2001085716A1 (en)	2001-11-15	2-piperidone compounds for the treatment of cancer
KR19990063850A (ko)	1999-07-26	Nmda 길항제로서의 테트라히드로퀴놀린
CN110461842A (zh)	2019-11-15	作为tnf活性调节剂的稠合五环咪唑衍生物
PH26783A (en)	1992-10-13	7-aryl and heteroaryl ethers of desacetylforskolin
WO2010004198A2 (fr)	2010-01-14	Derives anticancereux, leur preparation et leur application en therapeutique
KR19990016074A (ko)	1999-03-05	할로알콕시기를 함유하는 피롤로[3,2-c]퀴놀린
WO2009023669A1 (en)	2009-02-19	Substituted 5,6,7,8-tetrahydroquinoline derivatives, compositions, and methods of use thereof
JP3643916B2 (ja)	2005-04-27	新規な縮合インデン誘導体又はその塩
CN116600808A (zh)	2023-08-15	一类作为kras突变体g12c抑制剂的四氢萘啶类衍生物、其制备方法及其应用
US4847287A (en)	1989-07-11	Pure enantiomers of 4,5-disubstituted gamma-butyrolactams, and their use as antiamnestic agents
NZ227415A (en)	1991-12-23	(+)-4,9 dihydro-3-methyl-4-((4-methyl-1-piperazinyl) acetyl)-10h-thieno(3,4-b)(1,5)benzodiazepin-10-one and pharmaceutical compositions
CZ614690A3 (en)	1997-05-14	3-methoxy-4-£1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl) indol-3-ylmethyl\|-n-(2-methylphenylsulfonyl)benzamide, pharmaceutically acceptable salt thereof, process of their preparation and pharmaceutical compositions containing thereof
CZ177892A3 (en)	1993-02-17	AMINOMETHYL SUBSTITUTED 2,3-DIHYDROPYRAN(2,3-b)PYRIDINES, PROCESS OF THEIR PREPARATION AND THEIR USE IN MEDICAMENTS
JPH0749423B2 (ja)	1995-05-31	２−アルキルスルフイニル−４（３ｈ）−キナゾリノン誘導体、その製造方法およびそれを有効成分とする抗潰瘍薬
SK13582001A3 (sk)	2003-02-04	Spôsob prípravy kyseliny 3S-3-amino-3-arylpropiónovej a jej derivátov
US5177207A (en)	1993-01-05	7-aryl and heteroaryl ethers of desacetylforskolin