HRP20110045T1 - Sinteza acilaminoalkenilen amida korisnih kao antagonista supstance p - Google Patents
Sinteza acilaminoalkenilen amida korisnih kao antagonista supstance p Download PDFInfo
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- HRP20110045T1 HRP20110045T1 HR20110045T HRP20110045T HRP20110045T1 HR P20110045 T1 HRP20110045 T1 HR P20110045T1 HR 20110045 T HR20110045 T HR 20110045T HR P20110045 T HRP20110045 T HR P20110045T HR P20110045 T1 HRP20110045 T1 HR P20110045T1
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- 230000015572 biosynthetic process Effects 0.000 title claims 3
- 150000001408 amides Chemical class 0.000 title 1
- 239000003890 substance P antagonist Substances 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 34
- 125000006847 BOC protecting group Chemical group 0.000 claims abstract 23
- 125000005843 halogen group Chemical group 0.000 claims abstract 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 9
- 125000001424 substituent group Chemical group 0.000 claims abstract 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 9
- 238000000034 method Methods 0.000 claims abstract 8
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims abstract 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 5
- -1 C 1 -C 7 -alkyl Chemical group 0.000 claims abstract 5
- 239000012453 solvate Substances 0.000 claims abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 claims 2
- CZRKBWYUKKBUMS-HNNXBMFYSA-N (4r)-4-[[3,5-bis(trifluoromethyl)benzoyl]-methylamino]-5-(3,4-dichlorophenyl)pent-2-enoic acid Chemical compound C([C@@H](N(C)C(=O)C=1C=C(C=C(C=1)C(F)(F)F)C(F)(F)F)C=CC(O)=O)C1=CC=C(Cl)C(Cl)=C1 CZRKBWYUKKBUMS-HNNXBMFYSA-N 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/12—Nitrogen atoms not forming part of a nitro radical
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- Public Health (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Neurology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Postupak za pripremanje spojeva formule Iili njihovog solvata ili hidrata, gdjeR je fenil koji je nesupstituiran ili je supstituiran sa 1, 2 ili 3 supstituenta odabranih iz skupine koja sadrži halogen, C1-C7-alkil, trifluorometil, hidroksi i C1-C7-alkoksi; R1 je vodik ili C1-C7-alkil; R2 je vodik, C1-C7-alkil ili fenil koji je nesupstituiran ili je supstituiran sa 1, 2 ili 3 supstituenta odabranih iz skupine koja sadrži halogen, C1-C7-alkil, trifluorometil, hidroksi i C1-C7-alkoksi; R3 je fenil koji je nesupstituiran ili je supstituiran sa 1, 2 ili 3 supstituenta odabranih iz skupine koja sadrži halogen, C1-C7-alkil, trifluorometil, hidroksi i C1-C7-alkoksi, ili R3 je naftil, 1H-indol-3-il ili 1-C1-C7-alkil-indol-3-il; iR5 je C3-C8-cikloalkil, D-azacikloheptan-2-on-3-il ili L-azacikloheptan-2-on-3-il, naznačen time, da se postupak sastoji od sljedećih koraka: (a) reagiranje spoja formule IIgdje su R1 , R2 , R3 i R5 kako su određeni prethodno u ovom zahtjevu i T je BOC zaštitna skupina, pri čemu BOC je t-butoksikarbonil, s bazom za formiranje spoja formule IIIgdje su R1 , R2 , R3 i R5 kako su određeni prethodno u ovom zahtjevu, i (b) reagiranje spoja formule III gdje su R1 , R2 , R3 i R5 kako su određeni prethodno u ovom zahtjevu, sa spojem formule IVgdje R je fenil koji je nesupstituiran ili je supstituiran sa 1, 2 ili 3 supstituenta odabranih iz skupine koja sadrži halogen, C1-C7-alkil, trifluorometil, hidroksi i C1-C7-alkoksi, a X je halo, u prisutnosti baze za formiranje spoja formule I, te (c) opcijski, formiranje njegovog željenog solvata ili hidrata. Patent sadrži još 4 patentna zahtjeva.
Claims (5)
1. Postupak za pripremanje spojeva formule I
[image]
ili njihovog solvata ili hidrata, gdje
R je fenil koji je nesupstituiran ili je supstituiran sa 1, 2 ili 3 supstituenta odabranih iz skupine koja sadrži halogen, C1-C7-alkil, trifluorometil, hidroksi i C1-C7-alkoksi;
R1 je vodik ili C1-C7-alkil;
R2 je vodik, C1-C7-alkil ili fenil koji je nesupstituiran ili je supstituiran sa 1, 2 ili 3 supstituenta odabranih iz skupine koja sadrži halogen, C1-C7-alkil, trifluorometil, hidroksi i C1-C7-alkoksi;
R3je fenil koji je nesupstituiran ili je supstituiran sa 1, 2 ili 3 supstituenta odabranih iz skupine koja sadrži halogen, C1-C7-alkil, trifluorometil, hidroksi i C1-C7-alkoksi,
ili R3je naftil, 1H-indol-3-il ili 1-C1-C7-alkil-indol-3-il; i
R5je C3-C8-cikloalkil, D-azacikloheptan-2-on-3-il ili L-azacikloheptan-2-on-3-il,
naznačen time, da se postupak sastoji od sljedećih koraka:
(a) reagiranje spoja formule II
[image]
gdje su R1,R2,R3iR5kako su određeni prethodno u ovom zahtjevu i T je BOC zaštitna skupina, pri čemu BOC je t-butoksikarbonil,
s bazom za formiranje spoja formule III
[image]
gdje su R1 ,R2 ,R3iR5kako su određeni prethodno u ovom zahtjevu, i
(b) reagiranje spoja formule III gdje su R1 ,R2 ,R3iR5kako su određeni prethodno u ovom zahtjevu,
sa spojem formule IV
[image]
gdje R je fenil koji je nesupstituiran ili je supstituiran sa 1, 2 ili 3 supstituenta odabranih iz skupine koja sadrži halogen, C1-C7-alkil, trifluorometil, hidroksi i
C1-C7-alkoksi, a X je halo,
u prisutnosti baze za formiranje spoja formule I, te
(c) opcijski, formiranje njegovog željenog solvata ili hidrata.
2. Postupak prema zahtjevu 1, naznačen time, da je baza korištena u koraku (a) natrijev etoksid.
3. Postupak prema zahtjevu 1 ili zahtjevu 2, naznačen time, da je spoj formule II gdje su R1 ,R2 ,R3 ,R5i T kako su određeni u zahtjevu 1, pripravljen prema sljedećim koracima:
(i) reagiranje spoja formule V
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina,
sa 2.2-dimetil-[1,3]dioksan-4,6-dionom u prisutnosti baze za formiranje spoja formule VI
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina;
(ii) reagiranje spoja formule VI gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina,
s metanolom da se dobije spoj formule VII
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina;
(iii) reduciranje spoja formule VII gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina za formiranje spoja formule VIII
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina;
(iv) hidroliziranje spoja formule VIII gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina,
da se dobije odgovarajuća karboksilna kiselina formule IX
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina; i
(v) reagiranje spoja formule IX gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina,
sa spojem formule X
H2N-R5 X
gdje R5je C3-C8-cikloalkil, D-azacikloheptan-2-on-3-il ili L-azacikloheptan-2-on-3-il.
4. Postupak prema bilo kojem prethodnom zahtjevu, naznačen time, da spoj formule I je (4R)-4-[N'-metil-N'-(3,5-bistrifluorometil-benzoil)-amino]-4-(3,4-diklorobenzil)-but-2-enoička kiselina N-[R-epsilon-kaprolaktam-3-il]-amid hemihidrat.
5. Postupak prema zahtjevu 1 za pripremanje spoja formule I, koji je određen u zahtjevu 1, naznačen time, da postupak sadrži sljedeće korake:
(i) reagiranje spoja formule V
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina sa 2.2-dimetil-[1,3]dioksan-4,6-diona u prisutnosti baze za formiranje spoja formule VI
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina;
(ii) reagiranje spoja formule VI gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina, s metanolom da se dobije spoj formule VII
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina;
(iii) reduciranje spoja formule VII gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina, za formiranje spoja formule VIII
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina;
(iv) hidroliziranje spoja formule VIII gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina, da se dobije odgovarajuća karboksilna kiselina formule IX
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina;
(v) reagiranje spoja formule IX gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina, sa spojem formule X
H2N-R5 X
gdjeR5je C3-C8-cikloalkil, D-azacikloheptan-2-on-3-il ili L-azacikloheptan-2-on-3-il,
za formiranje spoja formule II
[image]
gdje su R1 ,R2iR3kako su određeni u zahtjevu 1, T je BOC zaštitna skupina, a R5je C3-C8-cikloalkil, D-azacikloheptan-2-on-3-il ili L-azacikloheptan-2-on-3-il;
(vi) opcijski, purificiranje spoja formule II gdje su R1 ,R2 , R3iR5kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina;
(vii) reagiranje spoja formule II gdje su R1 ,R2 , R3iR5kako su određeni u zahtjevu 1, a T je BOC zaštitna skupina,
s bazom za formiranje spoja formule III
[image]
gdje su R1 ,R2 , R3iR5kako su određeni u zahtjevu 1;
(viii) reagiranje spoja formule III gdje su R1 ,R2 , R3iR5kako su određeni u zahtjevu 1,
sa spojem formule IV
[image]
gdje R je fenil koji je nesupstituiran ili je supstituiran sa 1, 2 ili 3 supstituenta odabranih iz skupine koja sadrži halogen, C1-C7-alkil, trifluorometil, hidroksi i C1-C7-alkoksi, a X je halo, u prisutnosti baze za formiranje spoja formule I gdje su R, R1 ,R2 , R3iR5kako su određeni u zahtjevu 1; i
(ix) opcijski, formiranje željenog solvata ili hidrata.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0607532A GB0607532D0 (en) | 2006-04-13 | 2006-04-13 | Organic compounds |
| GB0610244A GB0610244D0 (en) | 2006-05-23 | 2006-05-23 | Organic compounds |
| PCT/EP2007/003213 WO2007118651A1 (en) | 2006-04-13 | 2007-04-11 | Synthesis of acylaminoalkenylene amides useful as substance p antagonists |
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| Publication Number | Publication Date |
|---|---|
| HRP20110045T1 true HRP20110045T1 (hr) | 2011-02-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110045T HRP20110045T1 (hr) | 2006-04-13 | 2011-01-21 | Sinteza acilaminoalkenilen amida korisnih kao antagonista supstance p |
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| Country | Link |
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| US (2) | US8008479B2 (hr) |
| EP (1) | EP2010498B1 (hr) |
| JP (1) | JP5208917B2 (hr) |
| KR (1) | KR20080108291A (hr) |
| AR (1) | AR060506A1 (hr) |
| AT (1) | ATE486853T1 (hr) |
| AU (1) | AU2007237482B2 (hr) |
| CA (1) | CA2645362C (hr) |
| CL (1) | CL2007001040A1 (hr) |
| CY (1) | CY1111294T1 (hr) |
| DE (1) | DE602007010269D1 (hr) |
| DK (1) | DK2010498T3 (hr) |
| EC (1) | ECSP088820A (hr) |
| GT (1) | GT200800209A (hr) |
| HK (1) | HK1125640A1 (hr) |
| HR (1) | HRP20110045T1 (hr) |
| JO (1) | JO2630B1 (hr) |
| MA (1) | MA30394B1 (hr) |
| MX (1) | MX2008013117A (hr) |
| MY (1) | MY145069A (hr) |
| NO (1) | NO20084783L (hr) |
| NZ (1) | NZ571142A (hr) |
| PE (1) | PE20071223A1 (hr) |
| PL (1) | PL2010498T3 (hr) |
| PT (1) | PT2010498E (hr) |
| RU (1) | RU2433122C2 (hr) |
| SI (1) | SI2010498T1 (hr) |
| TW (1) | TW200815358A (hr) |
| WO (1) | WO2007118651A1 (hr) |
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| CA2681628C (en) | 2007-03-16 | 2016-10-18 | Concert Pharmaceuticals, Inc. | Inhibitors of cholesterol ester transfer protein |
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|---|---|---|---|---|
| EA002348B1 (ru) | 1995-02-22 | 2002-04-25 | Новартис Аг | Соединения 1-арил-2-ациламиноэтана и их применение в качестве антагонистов нейрокинина, в частности нейрокинина 1 |
| MY132550A (en) * | 1996-08-22 | 2007-10-31 | Novartis Ag | Acylaminoalkenylene-amide derivatives as nk1 and nk2 antogonists |
| GB0010958D0 (en) * | 2000-05-05 | 2000-06-28 | Novartis Ag | Organic compounds |
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