DD251348A5 - Verfahren zur herstellung von heterozyklischen amidderivaten - Google Patents

Verfahren zur herstellung von heterozyklischen amidderivaten Download PDF

Info

Publication number: DD251348A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; group; ylmethyl; methyl; compound
Prior art date: 1985-04-17

Application number

DD86289307A

Other languages

German (de)

English (en)

Inventor

Federick J Brown

Peter R Bernstein

Viktor G Matassa

Ying K Yee

Original Assignee

Ici Americas Inc,Us

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.)

1985-04-17

Filing date

1986-04-17

Publication date

1987-11-11

1986-04-17 Application filed by Ici Americas Inc,Us filed Critical Ici Americas Inc,Us

1987-11-11 Publication of DD251348A5 publication Critical patent/DD251348A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 136
230000008569 process Effects 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title claims abstract description 12
150000001875 compounds Chemical class 0.000 claims abstract description 223
-1 heterocyclic amide Chemical class 0.000 claims abstract description 216
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 59
125000000217 alkyl group Chemical group 0.000 claims abstract description 51
239000001257 hydrogen Substances 0.000 claims abstract description 46
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 26
125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 13
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
230000002378 acidificating effect Effects 0.000 claims abstract description 3
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 66
238000006243 chemical reaction Methods 0.000 claims description 50
239000002253 acid Substances 0.000 claims description 36
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
150000002148 esters Chemical class 0.000 claims description 20
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
150000002431 hydrogen Chemical class 0.000 claims description 17
150000003254 radicals Chemical class 0.000 claims description 17
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 13
239000002168 alkylating agent Substances 0.000 claims description 12
229940100198 alkylating agent Drugs 0.000 claims description 12
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 12
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 12
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 12
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 11
239000002585 base Substances 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
238000000354 decomposition reaction Methods 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
150000002473 indoazoles Chemical class 0.000 claims description 10
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 7
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000001072 heteroaryl group Chemical group 0.000 claims description 7
125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
125000006302 indol-3-yl methyl group Chemical group [H]N1C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)C([H])([H])* 0.000 claims description 7
239000012948 isocyanate Substances 0.000 claims description 7
150000002513 isocyanates Chemical class 0.000 claims description 7
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
229910052702 rhenium Inorganic materials 0.000 claims description 7
229910021481 rutherfordium Inorganic materials 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
239000002841 Lewis acid Substances 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 6
150000007517 lewis acids Chemical class 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 5
229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 5
150000001565 benzotriazoles Chemical class 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
150000002475 indoles Chemical class 0.000 claims description 5
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
229910001923 silver oxide Inorganic materials 0.000 claims description 5
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 5
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 4
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
150000001556 benzimidazoles Chemical class 0.000 claims description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
150000002540 isothiocyanates Chemical class 0.000 claims description 4
125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical class C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 claims description 3
NCHRUPPPIFNPOD-UHFFFAOYSA-N 4-[[5-(cyclopentylcarbamoylamino)-1-methylindol-3-yl]methyl]-3-methoxy-n-(2-methylphenyl)sulfonylbenzamide Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)NC1CCCC1 NCHRUPPPIFNPOD-UHFFFAOYSA-N 0.000 claims description 3
YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 claims description 3
229910052782 aluminium Inorganic materials 0.000 claims description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
ZZGWEFLUSUHZRZ-UHFFFAOYSA-N cyclopentyl n-[3-[[4-(benzenesulfonylcarbamoyl)-2-methoxyphenyl]methyl]-1-methylindol-5-yl]carbamate Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 ZZGWEFLUSUHZRZ-UHFFFAOYSA-N 0.000 claims description 3
239000012024 dehydrating agents‎ Substances 0.000 claims description 3
125000006343 heptafluoro propyl group Chemical group 0.000 claims description 3
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
LOCAIGRSOJUCTB-UHFFFAOYSA-N indazol-3-one Chemical class C1=CC=C2C(=O)N=NC2=C1 LOCAIGRSOJUCTB-UHFFFAOYSA-N 0.000 claims description 3
150000002476 indolines Chemical class 0.000 claims description 3
125000002346 iodo group Chemical group I* 0.000 claims description 3
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims description 2
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 claims description 2
HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 claims description 2
YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical class C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 claims description 2
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims description 2
229940054051 antipsychotic indole derivative Drugs 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
150000008316 benzisoxazoles Chemical class 0.000 claims description 2
FBOSKQVOIHEWAX-UHFFFAOYSA-N benzothiazine Chemical class C1=CC=C2N=CCSC2=C1 FBOSKQVOIHEWAX-UHFFFAOYSA-N 0.000 claims description 2
125000002843 carboxylic acid group Chemical group 0.000 claims description 2
CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 claims description 2
150000001907 coumarones Chemical class 0.000 claims description 2
238000004132 cross linking Methods 0.000 claims description 2
MGMIPHDTLAASLA-UHFFFAOYSA-N cyclopentyl n-[3-[[4-(benzenesulfonylcarbamoyl)-2-methoxyphenyl]methyl]-1-benzothiophen-5-yl]carbamate Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=C1CC(C1=C2)=CSC1=CC=C2NC(=O)OC1CCCC1 MGMIPHDTLAASLA-UHFFFAOYSA-N 0.000 claims description 2
FCZVJRPADUYFBI-UHFFFAOYSA-N cyclopentyl n-[3-[[4-(benzenesulfonylcarbamoyl)-2-methoxyphenyl]methyl]benzimidazol-5-yl]carbamate Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=C1CN(C1=C2)C=NC1=CC=C2NC(=O)OC1CCCC1 FCZVJRPADUYFBI-UHFFFAOYSA-N 0.000 claims description 2
150000002440 hydroxy compounds Chemical class 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
229910001958 silver carbonate Inorganic materials 0.000 claims description 2
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 claims description 2
KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 claims description 2
150000003573 thiols Chemical class 0.000 claims description 2
239000011592 zinc chloride Substances 0.000 claims description 2
235000005074 zinc chloride Nutrition 0.000 claims description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 4
OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 claims 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
230000002152 alkylating effect Effects 0.000 claims 1
125000005605 benzo group Chemical group 0.000 claims 1
SKOXHEZNXXKBOY-UHFFFAOYSA-N cyclopentyl n-[3-[[4-(benzenesulfonylcarbamoyl)-2-methoxyphenyl]methyl]-1-methylindazol-5-yl]carbamate Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=C1CC(C1=C2)=NN(C)C1=CC=C2NC(=O)OC1CCCC1 SKOXHEZNXXKBOY-UHFFFAOYSA-N 0.000 claims 1
OQHBFPBWKNCKGR-UHFFFAOYSA-N cyclopentyl n-[3-[[4-(benzenesulfonylcarbamoyl)-2-methoxyphenyl]methyl]-1h-indol-5-yl]carbamate Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=C1CC(C1=C2)=CNC1=CC=C2NC(=O)OC1CCCC1 OQHBFPBWKNCKGR-UHFFFAOYSA-N 0.000 claims 1
JWIANSDZUAEDJO-UHFFFAOYSA-N cyclopentyl n-[4-[[4-(benzenesulfonylcarbamoyl)-2-methoxyphenyl]methyl]-2,3-dihydro-1,4-benzoxazin-6-yl]carbamate Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C=CC=CC=2)=CC=C1CN(C1=C2)CCOC1=CC=C2NC(=O)OC1CCCC1 JWIANSDZUAEDJO-UHFFFAOYSA-N 0.000 claims 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
125000004175 fluorobenzyl group Chemical group 0.000 claims 1
150000002460 imidazoles Chemical class 0.000 claims 1
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 8
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 abstract description 4
125000002947 alkylene group Chemical group 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
125000001475 halogen functional group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 216
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 189
239000000203 mixture Substances 0.000 description 105
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
239000000243 solution Substances 0.000 description 91
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
238000005481 NMR spectroscopy Methods 0.000 description 70
239000007787 solid Substances 0.000 description 62
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 58
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
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OTZRAYGBFWZKMX-JUDRUQEKSA-N leukotriene E4 Chemical compound CCCCCC=CCC=C\C=C\C=C\[C@@H](SC[C@H](N)C(O)=O)[C@@H](O)CCCC(O)=O OTZRAYGBFWZKMX-JUDRUQEKSA-N 0.000 description 1
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JPSNJFMTQIIVFG-UHFFFAOYSA-M lithium;ethanethiolate Chemical compound [Li+].CC[S-] JPSNJFMTQIIVFG-UHFFFAOYSA-M 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
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YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
LQXDABFFXSBEHF-UHFFFAOYSA-N methyl 3-[(6-amino-2,3-dihydro-1,4-benzoxazin-4-yl)methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2C3=CC(N)=CC=C3OCC2)=C1 LQXDABFFXSBEHF-UHFFFAOYSA-N 0.000 description 1
GHEFECHMYJWVSQ-UHFFFAOYSA-N methyl 3-[[6-(hexanoylamino)-2,3-dihydro-1,4-benzoxazin-4-yl]methyl]benzoate Chemical compound C12=CC(NC(=O)CCCCC)=CC=C2OCCN1CC1=CC=CC(C(=O)OC)=C1 GHEFECHMYJWVSQ-UHFFFAOYSA-N 0.000 description 1
OIZWUIAESOTUNM-UHFFFAOYSA-N methyl 3-methoxy-4-[(3-methoxy-6-nitroindazol-1-yl)methyl]benzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CN1C2=CC([N+]([O-])=O)=CC=C2C(OC)=N1 OIZWUIAESOTUNM-UHFFFAOYSA-N 0.000 description 1
SZTCOMGSHVHQSQ-UHFFFAOYSA-N methyl 3-methoxy-4-[(5-nitro-1-benzothiophen-3-yl)methyl]benzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC1=CSC2=CC=C([N+]([O-])=O)C=C12 SZTCOMGSHVHQSQ-UHFFFAOYSA-N 0.000 description 1
UZKUCUPQOOZWJC-UHFFFAOYSA-N methyl 3-methoxy-4-[(5-nitro-1h-indol-3-yl)methyl]benzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 UZKUCUPQOOZWJC-UHFFFAOYSA-N 0.000 description 1
IKJXWRDOCSSGNY-UHFFFAOYSA-N methyl 3-methoxy-4-[(6-nitrobenzimidazol-1-yl)methyl]benzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CN1C2=CC([N+]([O-])=O)=CC=C2N=C1 IKJXWRDOCSSGNY-UHFFFAOYSA-N 0.000 description 1
CAFQTCUBFQBEDZ-UHFFFAOYSA-N methyl 3-methoxy-4-[[1-(3-methylbut-2-enyl)-5-nitroindol-3-yl]methyl]benzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC1=CN(CC=C(C)C)C2=CC=C([N+]([O-])=O)C=C12 CAFQTCUBFQBEDZ-UHFFFAOYSA-N 0.000 description 1
LLEXCSBUSVRBCA-UHFFFAOYSA-N methyl 3-methoxy-4-methylbenzoate Chemical compound COC(=O)C1=CC=C(C)C(OC)=C1 LLEXCSBUSVRBCA-UHFFFAOYSA-N 0.000 description 1
CPXCDEMFNPKOEF-UHFFFAOYSA-N methyl 3-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C)=C1 CPXCDEMFNPKOEF-UHFFFAOYSA-N 0.000 description 1
YUQYQCYIZFMTFM-UHFFFAOYSA-N methyl 4-[(5-amino-1-cyclopentylindol-3-yl)methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC(C1=CC(N)=CC=C11)=CN1C1CCCC1 YUQYQCYIZFMTFM-UHFFFAOYSA-N 0.000 description 1
FFDQUHXGCGMVDT-UHFFFAOYSA-N methyl 4-[(5-amino-1-ethylindol-3-yl)methyl]-3-methoxybenzoate Chemical compound C12=CC(N)=CC=C2N(CC)C=C1CC1=CC=C(C(=O)OC)C=C1OC FFDQUHXGCGMVDT-UHFFFAOYSA-N 0.000 description 1
NLNCVNQSKSOZJY-UHFFFAOYSA-N methyl 4-[(5-amino-1-prop-2-ynylindol-3-yl)methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC1=CN(CC#C)C2=CC=C(N)C=C12 NLNCVNQSKSOZJY-UHFFFAOYSA-N 0.000 description 1
QZYRCKYKMJGJMA-UHFFFAOYSA-N methyl 4-[(6-amino-2,3-dihydro-1,4-benzoxazin-4-yl)methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CN1C2=CC(N)=CC=C2OCC1 QZYRCKYKMJGJMA-UHFFFAOYSA-N 0.000 description 1
CLNVHXPOUWWJFE-UHFFFAOYSA-N methyl 4-[2-[5-(cyclopentyloxycarbonylamino)-2-(methylamino)phenyl]-2-hydroxyiminoethyl]-3-methoxybenzoate Chemical compound C1=C(C(CC=2C(=CC(=CC=2)C(=O)OC)OC)=NO)C(NC)=CC=C1NC(=O)OC1CCCC1 CLNVHXPOUWWJFE-UHFFFAOYSA-N 0.000 description 1
LKWBXIIEIYGPNX-UHFFFAOYSA-N methyl 4-[[1-benzyl-5-(hexanoylamino)indol-3-yl]methyl]-3-methoxybenzoate Chemical compound C1=C(CC=2C(=CC(=CC=2)C(=O)OC)OC)C2=CC(NC(=O)CCCCC)=CC=C2N1CC1=CC=CC=C1 LKWBXIIEIYGPNX-UHFFFAOYSA-N 0.000 description 1
XZJMYCXXTDWDKR-UHFFFAOYSA-N methyl 4-[[1-cyclopentyl-5-(cyclopentyloxycarbonylamino)indol-3-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC(C1=CC(NC(=O)OC2CCCC2)=CC=C11)=CN1C1CCCC1 XZJMYCXXTDWDKR-UHFFFAOYSA-N 0.000 description 1
JXNMRDUQHALOCR-UHFFFAOYSA-N methyl 4-[[5-(2-ethylhexanoylamino)-1-methylindol-3-yl]methyl]-3-methoxybenzoate Chemical compound C12=CC(NC(=O)C(CC)CCCC)=CC=C2N(C)C=C1CC1=CC=C(C(=O)OC)C=C1OC JXNMRDUQHALOCR-UHFFFAOYSA-N 0.000 description 1
YZQVHUSWTAQOFI-UHFFFAOYSA-N methyl 4-[[5-(cyclopentyloxycarbonylamino)-1-(3-methylbut-2-enyl)indol-3-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC(C1=C2)=CN(CC=C(C)C)C1=CC=C2NC(=O)OC1CCCC1 YZQVHUSWTAQOFI-UHFFFAOYSA-N 0.000 description 1
XKDBWLXKEXMDIJ-UHFFFAOYSA-N methyl 4-[[5-(cyclopentyloxycarbonylamino)-1-(3-methylbutyl)indol-3-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC(C1=C2)=CN(CCC(C)C)C1=CC=C2NC(=O)OC1CCCC1 XKDBWLXKEXMDIJ-UHFFFAOYSA-N 0.000 description 1
CFQKOXAHEPUJBE-UHFFFAOYSA-N methyl 4-[[5-(cyclopentyloxycarbonylamino)-1-hexylindol-3-yl]methyl]-3-methoxybenzoate Chemical compound C12=CC(NC(=O)OC3CCCC3)=CC=C2N(CCCCCC)C=C1CC1=CC=C(C(=O)OC)C=C1OC CFQKOXAHEPUJBE-UHFFFAOYSA-N 0.000 description 1
ATNCAFJKGARVAJ-UHFFFAOYSA-N methyl 4-[[5-(cyclopentyloxycarbonylamino)-1-propylindol-3-yl]methyl]-3-methoxybenzoate Chemical compound C12=CC(NC(=O)OC3CCCC3)=CC=C2N(CCC)C=C1CC1=CC=C(C(=O)OC)C=C1OC ATNCAFJKGARVAJ-UHFFFAOYSA-N 0.000 description 1
CHMMNSJOQGGNBY-UHFFFAOYSA-N methyl 4-[[5-(cyclopentyloxycarbonylamino)-1h-indol-3-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC(C1=C2)=CNC1=CC=C2NC(=O)OC1CCCC1 CHMMNSJOQGGNBY-UHFFFAOYSA-N 0.000 description 1
ONZDXHKKSHJFGV-UHFFFAOYSA-N methyl 4-[[5-(hexanoylamino)-1-benzothiophen-3-yl]methyl]-3-methoxybenzoate Chemical compound C12=CC(NC(=O)CCCCC)=CC=C2SC=C1CC1=CC=C(C(=O)OC)C=C1OC ONZDXHKKSHJFGV-UHFFFAOYSA-N 0.000 description 1
PPBZAJPIBZRTGU-UHFFFAOYSA-N methyl 4-[[5-(hexanoylamino)-1-methylindol-3-yl]methyl]-3-methoxybenzoate Chemical compound C12=CC(NC(=O)CCCCC)=CC=C2N(C)C=C1CC1=CC=C(C(=O)OC)C=C1OC PPBZAJPIBZRTGU-UHFFFAOYSA-N 0.000 description 1
FVLXQUNPZKKYFF-UHFFFAOYSA-N methyl 4-[[5-(hexanoylamino)-1h-indol-3-yl]methyl]-3-methoxybenzoate Chemical compound C12=CC(NC(=O)CCCCC)=CC=C2NC=C1CC1=CC=C(C(=O)OC)C=C1OC FVLXQUNPZKKYFF-UHFFFAOYSA-N 0.000 description 1
KOUZRJIUAXSAJV-UHFFFAOYSA-N methyl 4-[[5-[(2-cyclopentylacetyl)amino]-1-methylindol-3-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)CC1CCCC1 KOUZRJIUAXSAJV-UHFFFAOYSA-N 0.000 description 1
CBMBUNJUFIVCOM-UHFFFAOYSA-N methyl 4-[[5-amino-1-(3-methylbut-2-enyl)indol-3-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC1=CN(CC=C(C)C)C2=CC=C(N)C=C12 CBMBUNJUFIVCOM-UHFFFAOYSA-N 0.000 description 1
LBPAHOABHCETRG-UHFFFAOYSA-N methyl 4-[[5-amino-1-(cyclopropylmethyl)indol-3-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC(C1=CC(N)=CC=C11)=CN1CC1CC1 LBPAHOABHCETRG-UHFFFAOYSA-N 0.000 description 1
QWKHQRFXZXAVIW-UHFFFAOYSA-N methyl 4-[[5-amino-1-[(3-cyanophenyl)methyl]indol-3-yl]methyl]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1CC(C1=CC(N)=CC=C11)=CN1CC1=CC=CC(C#N)=C1 QWKHQRFXZXAVIW-UHFFFAOYSA-N 0.000 description 1
QQPBPJLWTJHVIY-UHFFFAOYSA-N methyl 4-[[5-amino-1-[2-(dimethylamino)-2-oxoethyl]indol-3-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC1=CN(CC(=O)N(C)C)C2=CC=C(N)C=C12 QQPBPJLWTJHVIY-UHFFFAOYSA-N 0.000 description 1
XDOZKDRMTOZREV-UHFFFAOYSA-N methyl 4-[[5-amino-1-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]indol-3-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CC1=CN(CC(=O)OC(C)(C)C)C2=CC=C(N)C=C12 XDOZKDRMTOZREV-UHFFFAOYSA-N 0.000 description 1
KLUZTIJPXOQBIU-UHFFFAOYSA-N methyl 4-[[6-(2-ethylhexanoylamino)-2,3-dihydro-1,4-benzoxazin-4-yl]methyl]-3-methoxybenzoate Chemical compound C12=CC(NC(=O)C(CC)CCCC)=CC=C2OCCN1CC1=CC=C(C(=O)OC)C=C1OC KLUZTIJPXOQBIU-UHFFFAOYSA-N 0.000 description 1
HOGGATCYTRRMMM-UHFFFAOYSA-N methyl 4-[[6-(butoxycarbonylamino)benzimidazol-1-yl]methyl]-3-methoxybenzoate Chemical compound C12=CC(NC(=O)OCCCC)=CC=C2N=CN1CC1=CC=C(C(=O)OC)C=C1OC HOGGATCYTRRMMM-UHFFFAOYSA-N 0.000 description 1
JEAYOCMZILFFQD-UHFFFAOYSA-N methyl 4-[[6-(cyclopentyloxycarbonylamino)benzotriazol-1-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CN1C2=CC(NC(=O)OC3CCCC3)=CC=C2N=N1 JEAYOCMZILFFQD-UHFFFAOYSA-N 0.000 description 1
LSGOTNOBNNKDKY-UHFFFAOYSA-N methyl 4-[[6-[(2-cyclopentylacetyl)amino]-2,3-dihydro-1,4-benzoxazin-4-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CN1C2=CC(NC(=O)CC3CCCC3)=CC=C2OCC1 LSGOTNOBNNKDKY-UHFFFAOYSA-N 0.000 description 1
WMMBZARZISWBFL-UHFFFAOYSA-N methyl 4-[[6-[(2-cyclopentylacetyl)amino]-3-phenylmethoxyindazol-1-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CN1C2=CC(NC(=O)CC3CCCC3)=CC=C2C(OCC=2C=CC=CC=2)=N1 WMMBZARZISWBFL-UHFFFAOYSA-N 0.000 description 1
YRCJEXBWEJFYDU-UHFFFAOYSA-N methyl 4-[[6-[(2-cyclopentylacetyl)amino]benzimidazol-1-yl]methyl]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1CN1C2=CC(NC(=O)CC3CCCC3)=CC=C2N=C1 YRCJEXBWEJFYDU-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
KWERPWGWCMUCQE-UHFFFAOYSA-N n-(benzenesulfonyl)-4-[[5-(2-ethylhexanoylamino)-1-methylindol-3-yl]methyl]-3-methoxybenzamide Chemical compound C12=CC(NC(=O)C(CC)CCCC)=CC=C2N(C)C=C1CC(C(=C1)OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1 KWERPWGWCMUCQE-UHFFFAOYSA-N 0.000 description 1
VZUGBLTVBZJZOE-KRWDZBQOSA-N n-[3-[(4s)-2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide Chemical compound N1=C(N)N(C)C(=O)C[C@@]1(C)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CN=2)=C1 VZUGBLTVBZJZOE-KRWDZBQOSA-N 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 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
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
150000003140 primary amides Chemical class 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
239000010453 quartz Substances 0.000 description 1
229910052705 radium Inorganic materials 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000004043 responsiveness Effects 0.000 description 1
238000009666 routine test Methods 0.000 description 1
VFWRGKJLLYDFBY-UHFFFAOYSA-N silver;hydrate Chemical compound O.[Ag].[Ag] VFWRGKJLLYDFBY-UHFFFAOYSA-N 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
239000002002 slurry Substances 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
MFRRXGVCRJPOQI-UHFFFAOYSA-M sodium 1H-indole hydroxide Chemical compound N1C=CC2=CC=CC=C12.[OH-].[Na+] MFRRXGVCRJPOQI-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
210000005092 tracheal tissue Anatomy 0.000 description 1
238000012546 transfer Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
230000008728 vascular permeability Effects 0.000 description 1
230000002455 vasospastic effect Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD86289307A 1985-04-17 1986-04-17 Verfahren zur herstellung von heterozyklischen amidderivaten DD251348A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB858509882A GB8509882D0 (en)	1985-04-17	1985-04-17	Heterocyclic amide derivatives

Publications (1)

Publication Number	Publication Date
DD251348A5 true DD251348A5 (de)	1987-11-11

Family

ID=10577813

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86289307A DD251348A5 (de)	1985-04-17	1986-04-17	Verfahren zur herstellung von heterozyklischen amidderivaten

Country Status (6)

Country	Link
DD (1)	DD251348A5 (fr)
GB (1)	GB8509882D0 (fr)
GR (1)	GR861008B (fr)
LU (1)	LU90070I2 (fr)
ZA (1)	ZA862858B (fr)
ZM (1)	ZM4486A1 (fr)

1985
- 1985-04-17 GB GB858509882A patent/GB8509882D0/en active Pending
1986
- 1986-04-16 GR GR861008A patent/GR861008B/el unknown
- 1986-04-16 ZA ZA862858A patent/ZA862858B/xx unknown
- 1986-04-16 ZM ZM44/86A patent/ZM4486A1/xx unknown
- 1986-04-17 DD DD86289307A patent/DD251348A5/de unknown
1997
- 1997-05-28 LU LU90070C patent/LU90070I2/fr unknown

Also Published As

Publication number	Publication date
LU90070I2 (fr)	1997-07-23
GB8509882D0 (en)	1985-05-22
GR861008B (en)	1986-08-11
ZM4486A1 (en)	1986-10-29
ZA862858B (en)	1987-01-28

Legal Events

Date	Code	Title	Description
1995-03-02	RPI	Change in the person, name or address of the patentee (searches according to art. 11 and 12 extension act)
1995-03-02	RPV	Change in the person, the name or the address of the representative (searches according to art. 11 and 12 extension act)
2004-04-28	ASS	Change of applicant or owner	Owner name: ASTRAZENECA UK LIMITED, LONDON W1K 1LN Effective date: 20040128
2004-04-28	IF04	In force in the year 2004	Expiry date: 20060418

Publication	Publication Date	Title
KR900004384B1 (ko)	1990-06-23	복소환식 아미드 유도체 및 그 제조방법
DE60204718T2 (de)	2006-05-18	3-substituierte oxindol beta 3 agonisten
DE60211199T2 (de)	2007-02-01	3-substituierte oxindol-beta-3-agonisten
DK169541B1 (da)	1994-11-28	Amidisk indol- eller indazolderivat, fremgangsmåde til fremstilling heraf samt farmaceutisk middel indeholdende et sådant
DE60017376T2 (de)	2006-03-02	Carbaminsäurederivate und ihre verwendung als liganden von metabotropen glutamatrezeptoren
DE69206214T2 (de)	1996-07-04	Neue Arylethylaminderivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen.
DE69118388T2 (de)	1996-11-14	Substituierte bizyklische arylderivate mit selektiver leukotrien b4 antagonistischer wirkung
DE60215028T2 (de)	2007-03-15	Indol derivate als beta-3-adrenerge agonisten zur behandlung von typ 2 diabetes
CN101151246B (zh)	2011-04-13	1-苄基吲哚-2-甲酰胺衍生物
DE69110254T2 (de)	1996-01-04	Hydroxychinolonderivate.
DE69917478T2 (de)	2004-09-16	Piperazine und piperidine derivate
JPS63132889A (ja)	1988-06-04	キナゾリノン誘導体
EP2188253B1 (fr)	2012-03-07	Dérivés de l'indol-2-one disubstitués en 3, leur préparation et leur application en thérapeutique
DE3650567T2 (de)	1997-02-20	Medizinische Indol- und Indazol-Ketosulfonderivate
UA100192C2 (en)	2012-11-26	1-(arylsulfonyl)-4-(piperazin-1-yl)-1h-benzimidazoles as 5-hydroxytryptamine-6 ligands
DE68904342T2 (de)	1993-05-06	Cyclische amide.
DE68905216T2 (de)	1993-06-17	Hetera-aliphatische carboxamide.
DE3851907T2 (de)	1995-06-01	Aliphatische Carboxamide.
LU85254A1 (de)	1984-11-14	Verfahren zur herstellung von 3-(amino-oder subst.-amino)-4-(subst.-amino)-1,2,5-thiadiazol verbindungen
DE602006000102T2 (de)	2008-06-26	Indanyl-piperazinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
EP2940003A1 (fr)	2015-11-04	Dérivé d'amide d'acide cinnamique
EP0200947A1 (fr)	1986-11-12	Sels d'imidazolium substitué en position 1,3
DD251348A5 (de)	1987-11-11	Verfahren zur herstellung von heterozyklischen amidderivaten
DE69836427T2 (de)	2007-09-27	Heterozyclische ketonen als npy y5 antagonisten
DE69503186T2 (de)	1998-12-10	Tetrahydrobenz CD indole mit Serotonin-hemmende Aktivität