HUP0202193A2 - Eljárás egy spiro[ciklohexán-1,3'-[3'H]indolin]-2'-on-származék előállítására - Google Patents
Eljárás egy spiro[ciklohexán-1,3'-[3'H]indolin]-2'-on-származék előállítására Download PDFInfo
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- HUP0202193A2 HUP0202193A2 HU0202193A HUP0202193A HUP0202193A2 HU P0202193 A2 HUP0202193 A2 HU P0202193A2 HU 0202193 A HU0202193 A HU 0202193A HU P0202193 A HUP0202193 A HU P0202193A HU P0202193 A2 HUP0202193 A2 HU P0202193A2
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- HU
- Hungary
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- process according
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- july
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- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title claims description 26
- 125000003003 spiro group Chemical group 0.000 title abstract description 7
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 12
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 239000007864 aqueous solution Substances 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 16
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 9
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 claims description 4
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims description 4
- MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 3
- 150000008282 halocarbons Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims 2
- FQBFGERKZZFZNX-UHFFFAOYSA-N 4-(tert-butylcarbamoyl)-2-methoxybenzenesulfonyl chloride Chemical compound COC1=CC(C(=O)NC(C)(C)C)=CC=C1S(Cl)(=O)=O FQBFGERKZZFZNX-UHFFFAOYSA-N 0.000 abstract description 4
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 abstract description 2
- 102000002852 Vasopressins Human genes 0.000 abstract description 2
- 108010004977 Vasopressins Proteins 0.000 abstract description 2
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 abstract description 2
- 230000006103 sulfonylation Effects 0.000 abstract description 2
- 238000005694 sulfonylation reaction Methods 0.000 abstract description 2
- 229960003726 vasopressin Drugs 0.000 abstract description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 230000006181 N-acylation Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- PNDZEEPOYCVIIY-UHFFFAOYSA-N indo-1 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C=2N=C3[CH]C(=CC=C3C=2)C(O)=O)N(CC(O)=O)CC(O)=O)=C1 PNDZEEPOYCVIIY-UHFFFAOYSA-N 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- TWHXWYVOWJCXSI-UHFFFAOYSA-N phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O TWHXWYVOWJCXSI-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0202193A HUP0202193A2 (hu) | 2002-07-04 | 2002-07-04 | Eljárás egy spiro[ciklohexán-1,3'-[3'H]indolin]-2'-on-származék előállítására |
| PCT/HU2002/000075 WO2003011827A1 (en) | 2001-07-31 | 2002-07-25 | Process for the preparation of 3-spiro'cyclohexam-1,3'-'3h!indolin-2'-one! derivatives |
| DE60204154T DE60204154T2 (de) | 2001-07-31 | 2002-07-25 | Verfahren zur herstellung von 3 spiro'cyclohexan-1,3'-'3h!indolin-2'-on!derivaten |
| CA002453946A CA2453946C (en) | 2001-07-31 | 2002-07-25 | Process for the preparation of 3-spiro[cyclohexam-1,3'-[3h]indolin-2'-one] derivatives |
| AT02755383T ATE295350T1 (de) | 2001-07-31 | 2002-07-25 | Verfahren zur herstellung von 3 spiro'cyclohexan- 1,3'-'3höindolin-2'-onöderivaten |
| DK02755383T DK1421064T3 (da) | 2001-07-31 | 2002-07-25 | Fremgangsmåde til fremstilling af 3-spiro[cyclohexan-1,3'-[3H]indolin-2'-on] derivater |
| CNB028150589A CN1243736C (zh) | 2001-07-31 | 2002-07-25 | 3－螺环己烷－1,3'－'3h吲哚满－2'－酮衍生物的制备方法 |
| PL367292A PL205571B1 (pl) | 2001-07-31 | 2002-07-25 | Sposób wytwarzania pochodnych 3-spiro-cykloheksano-1,3'- (3H) indolin-2'-onu |
| BR0211445-3A BR0211445A (pt) | 2001-07-31 | 2002-07-25 | Processo para a preparação de derivados de 3-espiro' cicloexan-1,3' - '3h! indolin - 2'- ona! |
| PT02755383T PT1421064E (pt) | 2001-07-31 | 2002-07-25 | Processo para a preparacao de derivados de 3-espiro'ciclohexan-1,3'-'3h}indolin-2'-ona} |
| MXPA04000949A MXPA04000949A (es) | 2001-07-31 | 2002-07-25 | Proceso para la preparacion de derivados de 3-espiroæciclohexam-1,3æ-æ3h!indolin-2æ-ona!. |
| US10/485,133 US7619082B2 (en) | 2001-07-31 | 2002-07-25 | Process for the preparation of 3-spiro′cyclohexan-1,3′-′3H!indolin-2′-one! derivatives |
| HU0401203A HUP0401203A3 (en) | 2002-07-04 | 2002-07-25 | Process for the preparation of 3-spiro' cyclohexam-1,3'-'3h indolin-2' one derivatives |
| ES02755383T ES2240781T3 (es) | 2001-07-31 | 2002-07-25 | Procedimiento para la preparacion de derivados de 3-spiro(ciclohexan-1,3'-(3h)indolin-2'-ona). |
| JP2003517019A JP4520145B2 (ja) | 2001-07-31 | 2002-07-25 | ３−スピロ［シクロヘキサン−１，３’−［３ｈ］インドリン］−２’−オン誘導体の調製のための方法 |
| HR20040200A HRP20040200A2 (en) | 2001-07-31 | 2002-07-25 | Process for the preparation of 3-spiro'cyclohexam-1,3'-'3h ^indolin-2'-one^ derivatives |
| SI200230151T SI1421064T1 (sl) | 2001-07-31 | 2002-07-25 | Postopek za pripravo derivatov 3-spiro'cikloheksan-1,3'-'3H!indolin-2'-ona! |
| EP02755383A EP1421064B1 (en) | 2001-07-31 | 2002-07-25 | Process for the preparation of 3-spiro'cyclohexam-1,3'-'3h!indolin-2'-one! derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0202193A HUP0202193A2 (hu) | 2002-07-04 | 2002-07-04 | Eljárás egy spiro[ciklohexán-1,3'-[3'H]indolin]-2'-on-származék előállítására |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU0202193D0 HU0202193D0 (enExample) | 2002-09-28 |
| HUP0202193A2 true HUP0202193A2 (hu) | 2003-08-28 |
Family
ID=89980592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0202193A HUP0202193A2 (hu) | 2001-07-31 | 2002-07-04 | Eljárás egy spiro[ciklohexán-1,3'-[3'H]indolin]-2'-on-származék előállítására |
Country Status (1)
| Country | Link |
|---|---|
| HU (1) | HUP0202193A2 (enExample) |
-
2002
- 2002-07-04 HU HU0202193A patent/HUP0202193A2/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU0202193D0 (enExample) | 2002-09-28 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FA9A | Lapse of provisional patent protection due to relinquishment or protection considered relinquished |