NO317631B1 - Oksygeninneholdende heterocykliske forbindelser - Google Patents

Oksygeninneholdende heterocykliske forbindelser Download PDF

Info

Publication number: NO317631B1
Authority: NO; Norway
Prior art keywords: compound; substituted; methoxy; nmr; ppm
Prior art date: 1995-05-19

Application number

NO19970151A

Other languages

English (en)

Norwegian (no)

Other versions

NO970151L (no

NO970151D0 (no

Inventor

Fumio Suzuki

Takashi Kawakita

Etsuo Ohshima

Koji Yanagawa

Kyoichiro Iida

Rie Koike

Michio Ichimura

Haruhiko Manabe

Kenji Ohmori

Yoshisuke Nakasata

Original Assignee

Kyowa Hakko Kogyo Kk

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.)

1995-05-19

Filing date

1997-01-14

Publication date

2004-11-29

1997-01-14 Application filed by Kyowa Hakko Kogyo Kk filed Critical Kyowa Hakko Kogyo Kk

1997-01-14 Publication of NO970151D0 publication Critical patent/NO970151D0/no

1997-03-06 Publication of NO970151L publication Critical patent/NO970151L/no

2004-11-29 Publication of NO317631B1 publication Critical patent/NO317631B1/no

Links

229910052760 oxygen Inorganic materials 0.000 title claims abstract description 21
150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 11
239000001301 oxygen Substances 0.000 title claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
239000001257 hydrogen Substances 0.000 claims abstract description 47
125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 44
125000003118 aryl group Chemical group 0.000 claims abstract description 40
150000002431 hydrogen Chemical class 0.000 claims abstract description 40
125000000217 alkyl group Chemical group 0.000 claims abstract description 35
150000003839 salts Chemical class 0.000 claims abstract description 29
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
229910052799 carbon Inorganic materials 0.000 claims abstract description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
150000001721 carbon Chemical group 0.000 claims abstract description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 4
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims abstract description 4
-1 quinozolinyl Chemical group 0.000 claims description 35
125000003710 aryl alkyl group Chemical group 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 22
125000001589 carboacyl group Chemical group 0.000 claims description 9
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
230000002757 inflammatory effect Effects 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
239000000825 pharmaceutical preparation Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
208000026935 allergic disease Diseases 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
125000002971 oxazolyl group Chemical group 0.000 claims description 3
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
125000004193 piperazinyl group Chemical group 0.000 claims description 3
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000002098 pyridazinyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 3
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000001425 triazolyl group Chemical group 0.000 claims description 3
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims 2
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
125000006360 carbonyl amino methylene group Chemical group [H]N(C([*:1])=O)C([H])([H])[*:2] 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 908
238000000034 method Methods 0.000 description 295
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 270
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 185
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 183
239000000203 mixture Substances 0.000 description 178
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
238000002844 melting Methods 0.000 description 169
230000008018 melting Effects 0.000 description 169
239000000243 solution Substances 0.000 description 152
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 147
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 138
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 136
239000013078 crystal Substances 0.000 description 134
239000002904 solvent Substances 0.000 description 129
238000000921 elemental analysis Methods 0.000 description 126
238000003756 stirring Methods 0.000 description 117
239000000126 substance Substances 0.000 description 112
239000007787 solid Substances 0.000 description 111
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 99
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 96
238000006243 chemical reaction Methods 0.000 description 91
239000012044 organic layer Substances 0.000 description 87
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 86
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 78
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 76
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
238000010898 silica gel chromatography Methods 0.000 description 74
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 73
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
230000002829 reductive effect Effects 0.000 description 57
238000001816 cooling Methods 0.000 description 50
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
239000012442 inert solvent Substances 0.000 description 48
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 44
238000000605 extraction Methods 0.000 description 44
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 38
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 36
239000007864 aqueous solution Substances 0.000 description 36
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 36
230000008569 process Effects 0.000 description 33
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 29
238000010992 reflux Methods 0.000 description 28
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 26
238000009835 boiling Methods 0.000 description 26
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
239000012300 argon atmosphere Substances 0.000 description 23
229910052938 sodium sulfate Inorganic materials 0.000 description 23
235000011152 sodium sulphate Nutrition 0.000 description 23
XSIHTGSZVFKCNB-UHFFFAOYSA-N 2-[4-[(3,5-dichloropyridin-4-yl)carbamoyl]-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetic acid Chemical compound C1=2C(CC(O)=O)COC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl XSIHTGSZVFKCNB-UHFFFAOYSA-N 0.000 description 22
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 22
238000010438 heat treatment Methods 0.000 description 21
238000001914 filtration Methods 0.000 description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 19
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 19
229920006395 saturated elastomer Polymers 0.000 description 19
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 18
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 16
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 16
239000003377 acid catalyst Substances 0.000 description 16
239000002585 base Substances 0.000 description 16
239000000706 filtrate Substances 0.000 description 15
235000017557 sodium bicarbonate Nutrition 0.000 description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
238000004440 column chromatography Methods 0.000 description 14
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 14
238000012360 testing method Methods 0.000 description 14
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 14
238000007796 conventional method Methods 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 12
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 12
229910015900 BF3 Inorganic materials 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
238000004519 manufacturing process Methods 0.000 description 11
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 10
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
239000007858 starting material Substances 0.000 description 10
229940098779 methanesulfonic acid Drugs 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
QYOUBIYWOYGIQG-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(7-methoxy-2,2-dimethyl-3h-1-benzofuran-4-yl)ethanol Chemical compound C1=2CC(C)(C)OC=2C(OC)=CC=C1C(O)CC1=C(Cl)C=NC=C1Cl QYOUBIYWOYGIQG-UHFFFAOYSA-N 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000003814 drug Substances 0.000 description 8
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 8
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
206010006482 Bronchospasm Diseases 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
230000002401 inhibitory effect Effects 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
RIEKUNSZSAGWMV-UHFFFAOYSA-N methyl 2,2-diethyl-7-methoxy-3h-1-benzofuran-4-carboxylate Chemical compound COC1=CC=C(C(=O)OC)C2=C1OC(CC)(CC)C2 RIEKUNSZSAGWMV-UHFFFAOYSA-N 0.000 description 7
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
TVBIIGMNGQNEIR-UHFFFAOYSA-N 1-(7-methoxy-2,2-dimethyl-3h-1-benzofuran-4-yl)-2-pyridin-4-ylethanol Chemical compound C1=2CC(C)(C)OC=2C(OC)=CC=C1C(O)CC1=CC=NC=C1 TVBIIGMNGQNEIR-UHFFFAOYSA-N 0.000 description 6
BKZNPJJHZSUNLN-UHFFFAOYSA-N 1-(7-methoxy-3-methyl-2,3-dihydro-1-benzofuran-4-yl)-2-pyridin-4-ylethanol Chemical compound C1=2C(C)COC=2C(OC)=CC=C1C(O)CC1=CC=NC=C1 BKZNPJJHZSUNLN-UHFFFAOYSA-N 0.000 description 6
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 6
GNFGRSPDOZRGOT-UHFFFAOYSA-N 2-(3,5-dichloropyridin-4-yl)-1-(7-methoxy-3-methyl-2,3-dihydro-1-benzofuran-4-yl)ethanol Chemical compound C1=2C(C)COC=2C(OC)=CC=C1C(O)CC1=C(Cl)C=NC=C1Cl GNFGRSPDOZRGOT-UHFFFAOYSA-N 0.000 description 6
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
230000002152 alkylating effect Effects 0.000 description 6
230000007885 bronchoconstriction Effects 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
230000001413 cellular effect Effects 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
201000010099 disease Diseases 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
229940079593 drug Drugs 0.000 description 6
QSTNLQHRINHPQI-UHFFFAOYSA-N ethyl 2-[4-(cyclohexylcarbamoyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]acetate Chemical compound CCOC(=O)CC1COC(C(=CC=2)OC)=C1C=2C(=O)NC1CCCCC1 QSTNLQHRINHPQI-UHFFFAOYSA-N 0.000 description 6
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VYBYFHPHHSYOLH-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-2-methyl-3-(1,2,3,4-tetrahydroisoquinoline-1-carbonyl)-2,3-dihydro-1-benzofuran-4-carboxamide Chemical compound C1=2C(C(=O)C3C4=CC=CC=C4CCN3)C(C)OC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl VYBYFHPHHSYOLH-UHFFFAOYSA-N 0.000 description 1
FRTVVERWDKARQQ-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-2-pyridin-2-yl-1-benzofuran-4-carboxamide Chemical compound C1=2C=C(C=3N=CC=CC=3)OC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl FRTVVERWDKARQQ-UHFFFAOYSA-N 0.000 description 1
QRLVPRRVXWRUQN-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-2-pyridin-4-yl-1-benzofuran-4-carboxamide Chemical compound C1=2C=C(C=3C=CN=CC=3)OC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl QRLVPRRVXWRUQN-UHFFFAOYSA-N 0.000 description 1
RDDRBSCKIVSJDU-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-3-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-2,3-dihydro-1-benzofuran-4-carboxamide Chemical compound C1=2C(CC(=O)N3CCN(C)CC3)COC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl RDDRBSCKIVSJDU-UHFFFAOYSA-N 0.000 description 1
JMARLRBQRWIVSI-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-3-[2-oxo-2-(pyridin-2-ylmethylamino)ethyl]-2,3-dihydro-1-benzofuran-4-carboxamide Chemical compound C1=2C(CC(=O)NCC=3N=CC=CC=3)COC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl JMARLRBQRWIVSI-UHFFFAOYSA-N 0.000 description 1
NIPKLBWGSACZLK-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-3-[2-oxo-2-(pyridin-3-ylamino)ethyl]-2,3-dihydro-1-benzofuran-4-carboxamide Chemical compound C1=2C(CC(=O)NC=3C=NC=CC=3)COC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl NIPKLBWGSACZLK-UHFFFAOYSA-N 0.000 description 1
JZIVKAQTYRVWBU-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-3-[2-oxo-2-(pyridin-3-ylmethylamino)ethyl]-2,3-dihydro-1-benzofuran-4-carboxamide Chemical compound C1=2C(CC(=O)NCC=3C=NC=CC=3)COC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl JZIVKAQTYRVWBU-UHFFFAOYSA-N 0.000 description 1
TUWFLTAVVGQTQZ-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-3-[2-oxo-2-(pyridin-4-ylmethylamino)ethyl]-2,3-dihydro-1-benzofuran-4-carboxamide Chemical compound C1=2C(CC(=O)NCC=3C=CN=CC=3)COC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl TUWFLTAVVGQTQZ-UHFFFAOYSA-N 0.000 description 1
PPBVCLGXCHVIOU-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-3-[2-oxo-2-(pyrimidin-2-ylamino)ethyl]-2,3-dihydro-1-benzofuran-4-carboxamide Chemical compound C1=2C(CC(=O)NC=3N=CC=CN=3)COC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl PPBVCLGXCHVIOU-UHFFFAOYSA-N 0.000 description 1
QCKJCHWUWWQZMP-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-7-methoxy-3-phenyl-1-benzofuran-4-carboxamide Chemical compound C1=2C(C=3C=CC=CC=3)=COC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl QCKJCHWUWWQZMP-UHFFFAOYSA-N 0.000 description 1
QSVYCCGWISVICA-UHFFFAOYSA-N n-(3,5-dichloropyridin-4-yl)-8-methoxy-2,2-dimethyl-3,4-dihydrochromene-5-carboxamide Chemical compound C1=2CCC(C)(C)OC=2C(OC)=CC=C1C(=O)NC1=C(Cl)C=NC=C1Cl QSVYCCGWISVICA-UHFFFAOYSA-N 0.000 description 1
201000008383 nephritis Diseases 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
210000000440 neutrophil Anatomy 0.000 description 1
230000000414 obstructive effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
KGCNHWXDPDPSBV-UHFFFAOYSA-N p-nitrobenzyl chloride Chemical compound [O-][N+](=O)C1=CC=C(CCl)C=C1 KGCNHWXDPDPSBV-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 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
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-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
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
108010043671 prostatic acid phosphatase Proteins 0.000 description 1
HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
JQRYUMGHOUYJFW-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [Br-].[Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 JQRYUMGHOUYJFW-UHFFFAOYSA-N 0.000 description 1
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
210000001533 respiratory mucosa Anatomy 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
230000035939 shock Effects 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
229960002218 sodium chlorite Drugs 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000002269 spontaneous effect Effects 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
230000000638 stimulation Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
108060008037 tachykinin Proteins 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
SFLXUZPXEWWQNH-UHFFFAOYSA-K tetrabutylazanium;tribromide Chemical compound [Br-].[Br-].[Br-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC SFLXUZPXEWWQNH-UHFFFAOYSA-K 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
ISEIIPDWJVGTQS-UHFFFAOYSA-N tributylsilicon Chemical compound CCCC[Si](CCCC)CCCC ISEIIPDWJVGTQS-UHFFFAOYSA-N 0.000 description 1
ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
239000005052 trichlorosilane Substances 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
238000005303 weighing Methods 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- 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
- C07D405/14—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 three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Furan Compounds (AREA)
Pyrane Compounds (AREA)

NO19970151A 1995-05-19 1997-01-14 Oksygeninneholdende heterocykliske forbindelser NO317631B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP12153795		1995-05-19
JP25865195		1995-10-05
PCT/JP1996/001327 WO1996036624A1 (en)	1995-05-19	1996-05-20	Oxygen-containing heterocyclic compounds

Publications (3)

Publication Number	Publication Date
NO970151D0 NO970151D0 (no)	1997-01-14
NO970151L NO970151L (no)	1997-03-06
NO317631B1 true NO317631B1 (no)	2004-11-29

Family

ID=26458881

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19970151A NO317631B1 (no)	1995-05-19	1997-01-14	Oksygeninneholdende heterocykliske forbindelser

Country Status (13)

Country	Link
EP (1)	EP0771794B1 (de)
JP (1)	JP4172817B2 (de)
KR (1)	KR100445356B1 (de)
CN (1)	CN1163493C (de)
AT (1)	ATE325110T1 (de)
AU (1)	AU705690B2 (de)
CA (1)	CA2195755A1 (de)
DE (1)	DE69636086T2 (de)
DK (1)	DK0771794T3 (de)
ES (1)	ES2258775T3 (de)
NO (1)	NO317631B1 (de)
PT (1)	PT771794E (de)
WO (1)	WO1996036624A1 (de)

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WO1996036626A1 (de) *	1995-05-18	1996-11-21	Byk Gulden Lomberg Chemische Fabrik Gmbh	Cyclohexyldihydrobenzofurane
ES2191754T3 (es) *	1995-05-18	2003-09-16	Altana Pharma Ag	Fenil-dihidrobenzofuranos.
KR19990071894A (ko) *	1995-12-05	1999-09-27	마르크 젠너	벤조퓨란 카르복사미드 및 술폰아미드
CN1219171A (zh) *	1996-05-20	1999-06-09	达尔文发现有限公司	苯并呋喃甲酰胺及其治疗用途
WO1998007715A1 (de) *	1996-08-19	1998-02-26	Byk Gulden Lomberg Chemische Fabrik Gmbh	Novel benzofuran-4-carboxamides
WO1998022455A1 (en) *	1996-11-19	1998-05-28	Kyowa Hakko Kogyo Co., Ltd.	Oxygenic heterocyclic compounds
JP4219554B2 (ja) *	1997-10-01	2009-02-04	協和発酵キリン株式会社	ベンゾフラン誘導体
CA2317478A1 (en) *	1998-02-09	1999-08-12	Darwin Discovery Limited	Benzofuran-4-carboxamides and their therapeutic use
PT1095040E (pt) *	1998-07-06	2004-08-31	Altana Pharma Ag	Novos benzoxazoles com actividade inibidora da pde
MXPA01002102A (es)	1998-09-03	2003-02-24	Kyowa Hakko Kogyo Kk	Compuestos heterociclicos que contienen oxigeno.
EP1141278B1 (de) *	1998-12-30	2008-02-27	Oligos Etc. Inc.	Therapeutische pde4d phosphodiesterase inhibitoren
AU6315300A (en) *	1999-07-26	2001-02-13	Shionogi & Co., Ltd.	Benzene derivatives and immunopotentiating compositions or drug-sensitivity restoring agents containing the same
WO2003000697A1 (en) *	2001-06-22	2003-01-03	Takeda Chemical Industries, Ltd.	Furoisoquinoline derivative, process for producing the same, and use
DE10205274A1 (de) *	2002-02-08	2003-08-21	Boehringer Ingelheim Pharma	Neue Arzneimittelkompositionen enthaltend neben Anticholinergika heterocyclische Verbindungen
DE10216427A1 (de) *	2002-04-12	2003-10-23	Boehringer Ingelheim Pharma	Arzneimittelkompositionen enthaltend heterocyclische Verbindungen und ein neues Anticholinergikum
WO2004005276A1 (ja) *	2002-07-03	2004-01-15	Kyowa Hakko Kogyo Co., Ltd.	１，３−ベンゾジオキソール−２−スピロシクロアルカン誘導体の製造法
MXPA05009921A (es) *	2003-03-17	2005-11-04	Kyowa Hakko Kogyo Kk	Agentes terapeuticos y/o preventivos para enfermedades cutaneas cronicas.
WO2004087149A1 (ja) *	2003-03-31	2004-10-14	Kyowa Hakko Kogyo Co. Ltd.	医薬組成物
JPWO2004087146A1 (ja) *	2003-03-31	2006-06-29	協和醗酵工業株式会社	微粒子混合物の製造方法
JPWO2004087147A1 (ja) *	2003-03-31	2006-06-29	協和醗酵工業株式会社	肺疾患の治療および／または予防剤
WO2004096274A1 (ja) *	2003-03-31	2004-11-11	Kyowa Hakko Kogyo Co., Ltd.	気道内投与剤
JPWO2004087151A1 (ja) *	2003-03-31	2006-06-29	協和醗酵工業株式会社	医薬組成物
WO2004087150A1 (ja) *	2003-03-31	2004-10-14	Kyowa Hakko Kogyo Co. Ltd.	医薬組成物
JPWO2004087148A1 (ja) *	2003-03-31	2006-06-29	協和醗酵工業株式会社	肺疾患の治療および／または予防剤
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1996
- 1996-05-20 AT AT96915194T patent/ATE325110T1/de not_active IP Right Cessation
- 1996-05-20 PT PT96915194T patent/PT771794E/pt unknown
- 1996-05-20 KR KR1019970700326A patent/KR100445356B1/ko not_active Expired - Fee Related
- 1996-05-20 ES ES96915194T patent/ES2258775T3/es not_active Expired - Lifetime
- 1996-05-20 DE DE69636086T patent/DE69636086T2/de not_active Expired - Fee Related
- 1996-05-20 EP EP96915194A patent/EP0771794B1/de not_active Expired - Lifetime
- 1996-05-20 CN CNB961905298A patent/CN1163493C/zh not_active Expired - Fee Related
- 1996-05-20 WO PCT/JP1996/001327 patent/WO1996036624A1/ja not_active Ceased
- 1996-05-20 AU AU57029/96A patent/AU705690B2/en not_active Ceased
- 1996-05-20 JP JP53470896A patent/JP4172817B2/ja not_active Expired - Fee Related
- 1996-05-20 CA CA002195755A patent/CA2195755A1/en not_active Abandoned
- 1996-05-20 DK DK96915194T patent/DK0771794T3/da active
1997
- 1997-01-14 NO NO19970151A patent/NO317631B1/no unknown

Also Published As

Publication number	Publication date
EP0771794A1 (de)	1997-05-07
JP4172817B2 (ja)	2008-10-29
AU705690B2 (en)	1999-05-27
PT771794E (pt)	2006-09-29
NO970151L (no)	1997-03-06
CA2195755A1 (en)	1996-11-21
EP0771794B1 (de)	2006-05-03
KR970704724A (ko)	1997-09-06
HK1000785A1 (en)	2006-06-30
DK0771794T3 (da)	2006-09-11
NO970151D0 (no)	1997-01-14
ATE325110T1 (de)	2006-06-15
AU5702996A (en)	1996-11-29
CN1154697A (zh)	1997-07-16
CN1163493C (zh)	2004-08-25
ES2258775T3 (es)	2006-09-01
DE69636086D1 (de)	2006-06-08
EP0771794A4 (de)	1998-09-02
DE69636086T2 (de)	2006-11-30
WO1996036624A1 (en)	1996-11-21
KR100445356B1 (ko)	2004-11-12

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