HUP0303062A2 - New process and new intermediates for preparation of carboxamido-thiazole derivatives - Google Patents
New process and new intermediates for preparation of carboxamido-thiazole derivativesInfo
- Publication number
- HUP0303062A2 HUP0303062A2 HU0303062A HUP0303062A HUP0303062A2 HU P0303062 A2 HUP0303062 A2 HU P0303062A2 HU 0303062 A HU0303062 A HU 0303062A HU P0303062 A HUP0303062 A HU P0303062A HU P0303062 A2 HUP0303062 A2 HU P0303062A2
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- indole
- preparation
- methyl
- amino
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title 1
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- -1 thiazol-2-yl amino carbonyl indole derivatives Chemical class 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 239000012453 solvate Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 101710150887 Cholecystokinin A Proteins 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- WLVMWTBHFHMMPZ-UHFFFAOYSA-N n-carbamothioyl-1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)NC(=S)N)=CC2=C1 WLVMWTBHFHMMPZ-UHFFFAOYSA-N 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 239000000556 agonist Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229940032007 methylethyl ketone Drugs 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 abstract 1
- 229940116357 potassium thiocyanate Drugs 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Preparation of thiazol-2-yl amino carbonyl indole derivatives, their salts or solvates involves reacting N-(amino-thioxo-methyl)-1H-indole-2-carboxamide with an alpha -halogen-ketone. Preparation of thiazol-2-yl amino carbonyl indole derivative of formula (I), its salts or solvates involves reacting an N-(amino-thioxo-methyl)-1H-indole-2-carboxamide of formula (II) with an alpha -halogen-ketone of formula R8>-C(O)-CH(X)-R9>'> (III). (I) or its solvate is then transformed into its salt or liberated from its salt. [Image] R1>H or methyl; R2> - R5>R1>, T, OH, acetyloxy, methylthio, trifluoromethyl or amino; T : ethyl, methoxy, ethoxy or halo; R : H, -(CH2)nR6> or group of formula (a); R6>carboxyl or -COOR7>; R7>1-4C alkyl; n : 1 - 5; m : 0 or 1; R8>substituted phenyl of formula (b); R1>0>H or methoxy; R1>1>R1>, T or isopropyl; R1>2>R1>, ethyl, methoxy or halo; R1>1>+R1>2>methylenedioxy; R9>-CH2-R1>3>, -(CH2)2R1>3>, R'9> or 5-8C alkyl; R9>'>-S-CH2-R1>3> or -CH2-S-R1>3>; and R1>3>5-7C cycloalkyl; provided that R1>3> is 5-7C cycloalkyl when R1>0> - R1>2> is not H at the same time. Independent claims are also included for: (1) compounds of formulae (II) and (III); (2) preparation of (II) by transforming 1H-indole-2-carboxylic acid of formula (V) into 1H-indole-2-carboxylic acid halogenide of formula (VI), reacting (VI) with potassium-thiocyanate in the presence of a diprotic-aprotic solvent (preferably acetone or methyl-ethyl-ketone) and reacting the isothiocyanate of formula (VIII) with ammonia or ammonium hydroxide; and (3) preparation of (III) by acylating a methoxy benzene of formula (X) with an acid-chloride of formula Cl-C(O)-CH2-(CH2)o-S-(CH2)p-R1>4> (XI) in the presence of a Lewis acid (preferably titanium-tetrachloride or aluminum chloride), and halogenating R8>-C(O)-CH2-R'9> (IX). [Image] Hlg : halo. R1>4>5-7C cycloalkyl; o : 1 or 2; and p : 0 or 1. ACTIVITY : None given. MECHANISM OF ACTION : Cholecystokinin A (CCK-A) agonist.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0303062A HUP0303062A2 (en) | 2000-11-28 | 2001-11-27 | New process and new intermediates for preparation of carboxamido-thiazole derivatives |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0004741A HUP0004741A2 (en) | 2000-11-28 | 2000-11-28 | Chemical process for the preparation of thiazole derivatives and new intermediate |
| PCT/HU2001/000121 WO2002044150A1 (en) | 2000-11-28 | 2001-11-27 | Chemical process and new intermediates |
| HU0303062A HUP0303062A2 (en) | 2000-11-28 | 2001-11-27 | New process and new intermediates for preparation of carboxamido-thiazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUP0303062A2 true HUP0303062A2 (en) | 2003-12-29 |
Family
ID=89981653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0303062A HUP0303062A2 (en) | 2000-11-28 | 2001-11-27 | New process and new intermediates for preparation of carboxamido-thiazole derivatives |
Country Status (1)
| Country | Link |
|---|---|
| HU (1) | HUP0303062A2 (en) |
-
2001
- 2001-11-27 HU HU0303062A patent/HUP0303062A2/en unknown
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