RU2003124068A - Способ получения (3-циано-1h-индол-7-ил) (4-фторфенетил)-пиперазин-1-ил) метанона и его солей - Google Patents
Способ получения (3-циано-1h-индол-7-ил) (4-фторфенетил)-пиперазин-1-ил) метанона и его солей Download PDFInfo
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- RU2003124068A RU2003124068A RU2003124068/04A RU2003124068A RU2003124068A RU 2003124068 A RU2003124068 A RU 2003124068A RU 2003124068/04 A RU2003124068/04 A RU 2003124068/04A RU 2003124068 A RU2003124068 A RU 2003124068A RU 2003124068 A RU2003124068 A RU 2003124068A
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- Prior art keywords
- formula
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- cyano
- indole
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- 150000003839 salts Chemical class 0.000 title claims 9
- -1 (4-fluorophenethyl) -piperazin-1-yl Chemical group 0.000 title claims 4
- 238000004519 manufacturing process Methods 0.000 title 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- FDASYGXNFLWEMM-UHFFFAOYSA-N 3-cyano-1h-indole-7-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1NC=C2C#N FDASYGXNFLWEMM-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- LODHVDKKTUZVDK-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]piperazine Chemical compound C1=CC(F)=CC=C1CCN1CCNCC1 LODHVDKKTUZVDK-UHFFFAOYSA-N 0.000 claims 3
- 150000002923 oximes Chemical class 0.000 claims 3
- CBTITARLOCZPDU-UHFFFAOYSA-N 1h-indole-2-carbonitrile Chemical compound C1=CC=C2NC(C#N)=CC2=C1 CBTITARLOCZPDU-UHFFFAOYSA-N 0.000 claims 2
- AQRLDDAFYYAIJP-UHFFFAOYSA-N Pruvanserin Chemical compound C1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C=3NC=C(C=3C=CC=2)C#N)CC1 AQRLDDAFYYAIJP-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000007098 aminolysis reaction Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000022244 formylation Effects 0.000 claims 1
- 238000006170 formylation reaction Methods 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
Classifications
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- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/04—Preparation of lactams from or via oximes by Beckmann rearrangement
- C07D201/06—Preparation of lactams from or via oximes by Beckmann rearrangement from ketones by simultaneous oxime formation and rearrangement
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
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- Pain & Pain Management (AREA)
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- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Toxicology (AREA)
- Vascular Medicine (AREA)
- Anesthesiology (AREA)
- Nutrition Science (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (11)
1. Способ получения (3-циано-1Н-индол-7-ил)[4-(4-фторфенетил)пиперазин-1-ил]метанона формулы I
и его солей, характеризующийся тем, что
(1) сложный эфир индола формулы II
в которой R представляет собой алкильную группу, которая имеет от 1 до 6 атомов углерода или арилалкил, подвергают формилированию,
(2) формил сложного эфира формулы III
в которой R является таким как определено выше,
полученный на стадии (1) вводят во взаимодействие с гидроксиламином с образованием производного оксима формулы IV
в которой R является таким как определено выше,
(3) оксим формулы IV превращают в сложный эфир цианоиндола формулы V
в которой R имеет одно из значений приведенных выше,
(4) сложный эфир формулы V подвергают омылению с получением 3-циано-1Н-индол-7-карбоновой кислоты,
(5) 3-циано-1Н-индол-7-карбоновую кислоту вводят во взаимодействие с 1-[2-(4-фторфенил)этил]пиперазином или его солями с получением соединения формулы I, и
(6) полученной основание формулы I превращают в одно из его солей путем обработки кислотой.
2. Способ в соответствии с пунктом 1, отличающийся тем, что стадии (1)-(3) проводят в одном реакторе.
3. Способ в соответствии с пунктом 1, отличающийся тем, что на стадии (4) сложный эфир формулы V превращают в соединение формулы I путем аминолиза используя 1-[2-(4-фторфенил)этил]пиперазин или одну из его солей.
4. Способ в соответствии с пунктом 1, отличающийся тем, что 3-циано-1H-индол-7-карбоновую кислоту получают путем галогенирования сложного эфира индола формулы II
и в соответствии с пунктом 1 получают соединение формулы VI
в которой R представляет собой алкильную группу, которая имеет от 1 до 6 атомов углерода или арилалкил; и
Hal представляет собой Cl, Вr или I, с последующим цианированием последнего.
5. Способ в соответствии с одним или большим количеством пунктов 1-4, характеризующийся тем, что R представляет собой этил.
6. Способ в соответствии с одним или большим количеством пунктов 1-5, отличающийся тем, что 1-[2-(4-фторфенил)этил]пиперазин используют в виде дигидрохлорида.
7. Способ в соответствии с одним или большим количеством пунктов 1-6, отличающийся тем, что основание, (3-циано-1Н-индол-7-ил)[4-(4-фторфенетил)пиперазин-1-ил]метанон, превращают в его гидрохлорид.
8. Производные оксима формулы IV
в которой R представляет собой алкильную группу, которая имеет от 1 до 6 атомов углерода, или арилалкил, и их соли.
9. Сложные эфиры цианоиндола формулы V
в которой R представляет собой алкильную группу, которая имеет от 1 до 6 атомов углерода, или арилалкил, и их соли.
10. 3-Циано-1Н-индол-7-карбоновая кислота и ее соли.
11. Соединения формулы VI
в которой R представляет собой алкильную группу, которая имеет от 1 до 6 атомов углерода, или арилалкил; и
Hal представляет собой Cl, Вr или I, и их соли.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10102944A DE10102944A1 (de) | 2001-01-23 | 2001-01-23 | Verfahren zur Herstellung von (3-Cyan-1H-indol-7-yl)-[4-(4-fluorphenethyl)-piperazin-1-yl]-methanon und dessen Salzen |
| DE10102944.6 | 2001-01-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2003124068A true RU2003124068A (ru) | 2005-01-10 |
| RU2295519C2 RU2295519C2 (ru) | 2007-03-20 |
Family
ID=7671481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003124068/04A RU2295519C2 (ru) | 2001-01-23 | 2001-12-21 | Способ получения (3-циано-1h-индол-7-ил)[4-(4-фторфенетил)пиперазин-1-ил] метанона и его солей |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US7312342B2 (ru) |
| EP (1) | EP1353906B1 (ru) |
| JP (1) | JP4215195B2 (ru) |
| KR (1) | KR100820763B1 (ru) |
| CN (1) | CN1213029C (ru) |
| AR (1) | AR032261A1 (ru) |
| AT (1) | ATE269849T1 (ru) |
| AU (1) | AU2002219220B2 (ru) |
| BR (1) | BR0116816A (ru) |
| CA (1) | CA2435426C (ru) |
| CZ (1) | CZ20032202A3 (ru) |
| DE (2) | DE10102944A1 (ru) |
| DK (1) | DK1353906T3 (ru) |
| EC (1) | ECSP034737A (ru) |
| ES (1) | ES2223738T3 (ru) |
| HU (1) | HUP0401039A3 (ru) |
| IL (2) | IL157061A0 (ru) |
| MX (1) | MXPA03006534A (ru) |
| MY (1) | MY126252A (ru) |
| NZ (1) | NZ527779A (ru) |
| PL (1) | PL209416B1 (ru) |
| PT (1) | PT1353906E (ru) |
| RU (1) | RU2295519C2 (ru) |
| SK (1) | SK286565B6 (ru) |
| TR (1) | TR200402142T4 (ru) |
| TW (1) | TW588044B (ru) |
| UA (1) | UA74039C2 (ru) |
| WO (1) | WO2002059092A1 (ru) |
| ZA (1) | ZA200306540B (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10246357A1 (de) * | 2002-10-04 | 2004-04-15 | Merck Patent Gmbh | Verwendung von 5-HT2Rezeptorantagonisten |
| DE102004047517A1 (de) * | 2004-09-28 | 2006-03-30 | Merck Patent Gmbh | Neuartige Kristallform von (3-Cyan-1H-indol-7-yl)-[4-(4-fluorphenethyl)-piperazin-1-yl]-methanon, Hydrochlorid |
| CN101437793B (zh) * | 2006-05-05 | 2012-08-22 | 默克专利股份有限公司 | 结晶的（3-氰基-1h-吲哚-7-基）-[4-（4-氟苯乙基）哌嗪-1-基]甲酮磷酸盐 |
| CA2652215A1 (en) * | 2006-05-05 | 2007-11-15 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Crystalline (3-cyano-1h-indol-7-yl)-[4-(4-fluorophenethyl)piperazin-1-yl]methanone phosphate |
| CN102816104B (zh) * | 2012-08-30 | 2014-05-21 | 浙江大学 | 一种3-氰基吲哚类化合物的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH421107A (de) * | 1963-06-04 | 1966-09-30 | Sandoz Ag | Verfahren zur Herstellung neuer heterocyclischer Verbindungen |
| CA2084531A1 (en) * | 1991-12-19 | 1993-06-20 | David W. Smith | Antimigraine 4-pyrimidinyl and pyridinyl derivatives of indol-3yl-alkyl piperazines |
-
2001
- 2001-01-23 DE DE10102944A patent/DE10102944A1/de not_active Withdrawn
- 2001-12-21 HU HU0401039A patent/HUP0401039A3/hu unknown
- 2001-12-21 PL PL364392A patent/PL209416B1/pl not_active IP Right Cessation
- 2001-12-21 KR KR1020037009645A patent/KR100820763B1/ko not_active Expired - Fee Related
- 2001-12-21 BR BR0116816-9A patent/BR0116816A/pt not_active Application Discontinuation
- 2001-12-21 US US10/466,991 patent/US7312342B2/en not_active Expired - Fee Related
- 2001-12-21 EP EP01273449A patent/EP1353906B1/en not_active Expired - Lifetime
- 2001-12-21 AT AT01273449T patent/ATE269849T1/de active
- 2001-12-21 CN CNB018221882A patent/CN1213029C/zh not_active Expired - Fee Related
- 2001-12-21 ES ES01273449T patent/ES2223738T3/es not_active Expired - Lifetime
- 2001-12-21 PT PT01273449T patent/PT1353906E/pt unknown
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