WO2003035057A1 - Inhibitors of dipeptidyl peptidase iv - Google Patents
Inhibitors of dipeptidyl peptidase iv Download PDFInfo
- Publication number
- WO2003035057A1 WO2003035057A1 PCT/GB2002/004764 GB0204764W WO03035057A1 WO 2003035057 A1 WO2003035057 A1 WO 2003035057A1 GB 0204764 W GB0204764 W GB 0204764W WO 03035057 A1 WO03035057 A1 WO 03035057A1
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- Prior art keywords
- alkyl
- compound according
- butyloxycarbonyl
- vacuo
- residue
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- 0 CN(*)Cc1c(*)nccc1 Chemical compound CN(*)Cc1c(*)nccc1 0.000 description 2
- CALTZIJUSZODSD-IBGZPJMESA-N CN(CCC[C@@H](C(N1CSCC1)=O)N)Cc1cccc2c1cccc2 Chemical compound CN(CCC[C@@H](C(N1CSCC1)=O)N)Cc1cccc2c1cccc2 CALTZIJUSZODSD-IBGZPJMESA-N 0.000 description 1
- MZDVNJMSXVFWOS-ZDUSSCGKSA-N N[C@@H](CCCCNc1nc(O)nc(Nc(cc(cc2)Cl)c2Cl)n1)C(N1CSCC1)=O Chemical compound N[C@@H](CCCCNc1nc(O)nc(Nc(cc(cc2)Cl)c2Cl)n1)C(N1CSCC1)=O MZDVNJMSXVFWOS-ZDUSSCGKSA-N 0.000 description 1
- BBKICKXCBMITOU-UHFFFAOYSA-N O=C(CNCCNCC1CCCCC1)N1CCSCC1 Chemical compound O=C(CNCCNCC1CCCCC1)N1CCSCC1 BBKICKXCBMITOU-UHFFFAOYSA-N 0.000 description 1
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
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- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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Definitions
- the present invention relates to novel compounds that are inhibitors of post-proline aminopeptidases.
- the compounds are useful as antiproliferative agents and in the treatment of, inter alia, type 2 diabetes and impaired glucose tolerance.
- X 3 , X 4 and X 5 are either nitrogen N or CH, provided that at least two of X 3 , X 4 and X 5 are N.
- X 6 is either O or NH.
- R 2 is either H or alkyl.
- R 3 is selected from H, CI, OH, O- alkyl, NH 2 , NH-alkyl and N(alkyl) 2 .
- R 4 , R 5 , R 6 , R 7 and R 8 are selected from H, Br, CI, F, CF 3 , alkyl, acyl, OH, O-alkyl, NH 2 , NH-alkyl, N(alkyl) 2 , N0 2 , NH-acyl, C0 2 H, C0 2 -alkyl, CONH 2 , CONH-alkyl, CON(alkyl) 2 and CN.
- X 7 is CH 2 , O, S or NH.
- R 9 is either H or alkyl.
- R 18 is H, alkyl, aryl, OH, O-alkyl, NH 2 , NH-alkyl or N(alkyl) 2
- R 19 is H, alkyl, aryl, F, CI, Br, CF 3 , OH, O-alkyl, NH 2 , NH-alkyl or N(alkyl) 2
- the integers d and e are 0, 1 , 2 or 3 such that d+e is 3, 4 or 5, and f is 1 , 2 or 3.
- X 1 may not be S or CH 2 if b is 1.
- Preferred compositions are inhibitors of non-membrane associated post-proline cleaving proteases. The most preferred compositions are selective for non-membrane associated proteases (e.g. for example inhibitors of one or more of QPP, DPP-8 and/or DPP-9).
- the group R 1 is either a hydrogen atom H or a nitrile group CN.
- the group X 1 is selected from an oxygen atom O, a sulphur atom S, a methylene group CH 2 , a monofluoromethylene group CHF.a difluoromethylene group CF 2 , an ethylidene group CH(CH 3 ), a 2-propylidene group C(CH 3 ) 2 and a cyanomethylene group CH(CN).
- the integer b is either 1 or 2, such that the nitrogen-containing ring has 5 or 6 members.
- the group G 3 is selected from a group according to general formula 2, a group according to general formula 3 and a group according to general formula 4.
- R 4 , R 5 , R 6 , R 7 and R 8 are independently selected from H, Br, CI, F, CF 3 , alkyl, acyl, OH, 0- alkyl, NH 2 , NH-alkyl, N(alkyl) 2 , N0 2 , NH-acyl, C0 2 H, C0 2 -alkyl, CONH 2 , CONH-alkyl, CON(alkyl) 2 and CN.
- alkenyl denotes monounsaturated hydrocarbon groups with between 2 and 10 carbon atoms, including straight-chain, branched and mono- and polycycloalkenyl groups, such as vinyl, allyl, methallyl, cyclohex-3-enyl and the like.
- aryl groups may optionally be substituted with up to three groups independently selected from alkyl, OH, O-alkyl, CI, F, Br, NH 2 , NH-alkyl, N(alkyl) 2 , C0 2 H, C0 2 -alkyl, CONH 2 , CONH-alkyl, CON(alkyl) 2 , N0 2 and CN.
- aralkyl denotes alkyl groups that are substituted by, or fused to, one or more aryl groups, including benzyl, phenethyl, indanyl, fluorenyl and the like.
- polyfluoroalkyl denotes an alkyl group wherein all the hydrogen atoms on one or more of the carbon atoms are replaced by fluorine atoms, including trifluoromethyl, 2,2,2-trifluoroethyl and the like.
- R 1 is H.
- R 1 is CN
- X 1 is CH 2 .
- X 1 is S.
- b is 2.
- a is 0.
- a is 1.
- a is 1 and X 2 is CH 2 .
- a is 2 and X 2 is CH 2 .
- the compound is a compound according to general formula 10.
- the compound is a compound according to general formula 11.
- the compound is a compound according to general formula 12.
- the compound is a compound according to general formula 13.
- the compounds of the present invention can be prepared by methods generally known in the art and illustrated in the following non-limiting examples.
- (2S)-1-( / ⁇ -(terf-Butyloxycarbonyl)- ⁇ / ⁇ , ⁇ -(dicinnamyl)-L-lysinyl)pyrrolidine-2- carbonitrile (32mg, 0.057mmol) was dissolved in 4M HCI/dioxan (20mL). After 1 h at room temperature the solvent was removed in vacuo. The residue was lyophilised from water to give a white solid identified as (2S)-1-[/ ⁇ f,/ ⁇ T-(dicinnamyl)-L- lysinyl]pyrrolidine-2-carbonitrile dihydrochloride (37mg, 0.053mmol, 93%).
- (2S)-1-( ⁇ / ⁇ -(tert-Butyloxycarbonyl)- ⁇ / ⁇ ,/ ⁇ -(dicinnamyl)-L-ornithinyl)pyrrolidine-2- carbonitrile (67mg, 0.12mmol) was dissolved in 4M HCI/dioxan (20mL). After 1h at room temperature the solvent was removed in vacuo. The residue was lyophilised from water to give a white solid identified as (2S)-1-[/ ⁇ T,/ ⁇ T-(dicinnamyl)-L- ornithinyl]pyrrolidine-2-carbonitrile dihydrochloride (82mg, 0.12mmol, 100%).
- (2S)-1-( ⁇ / ⁇ -(tert-Butyloxycarbonyl)- ⁇ / ⁇ -(cinnamyl)-L-ornithinyl)pyrrolidine-2-carbonitrile (71mg, 0.17mmol). was dissolved in 4M HCI/dioxan (20mL). After 1h at room temperature the solvent was removed in vacuo. The residue was lyophilised from water to give a white solid identified as (2S)-1-[ ⁇ T-(cinnamyl)-L-ornithinyl]pyrrolidine-2- carbonitrile dihydrochloride (91mg, 0.16mmol, 100%).
- 3-( ⁇ /°-(tert-Butyloxycarbonyl)-L-lysinyl)thiomorpholine (150mg, 0.45mmol) was dissolved in methanol (25mL). To this solution was added 3- cyclohexenecarboxaldehyde (400mg, 0.45mmol). After 30mins sodium triacetoxyborohydride (150mg, 0.71 mmol) was added. After 18h at room temperature the solvent was removed in vacuo and the residue was taken up in chloroform (70mL).
- 3-Chloroaniline was dissolved in xylene. 2-Aminonicotinic acid was added. The reaction mixture was heated at 150 °C for 18 hours after which time the reaction mixture was diluted with ethyl acetate giving an off-white solid identified as 3- chloroanilinonicotinic acid.
- Cyanuric chloride (1.844g, 10mmol) was dissolved in acetonitrile (20mL). The solution was cooled to -20 °C. A solution of 2,5-dichloroaniline (1.62g, 10mmol) and triethylamine (1.0g, 10mmol) was slowly added. After 1 hour at -20 °C the solvent was removed in vacuo and the residue was taken up in ethyl acetate (150mL). The solution was washed with water (1 x 50mL) and brine (1 x 50mL), dried (Na 2 S0 4 ) and evaporated in vacuo.
- N-(fert-Butyloxycarbonyl)-3-hydroxypyrrolidine (21.0g, 10.7mmol) was dissolved in CH 2 CI 2 (30ml).
- (Diethylamino)sulphur trifluoride (1.72g, 10.7mmol) was added to this solution at -78 °C.
- the mixture was stirred for 18 hours at -78 °C to room temperature then the reaction mixture was carefully poured into sat. NaHC0 3 (100ml) and stirred for 15min and extracted with CH 2 CI 2 .
- the organic extract was washed with water and brine, dried (Na 2 S0 4 ) and evaporated in vacuo to give an orange oil.
- N-2 ' -(fert-Butyloxycarbonyl)-N-(2 " -(9-fluorenylmethyloxycarbonyI aminoethyl)-glycine (2. ⁇ g, ⁇ .7mmol) was dissolved in CH 2 Cl 2 /DMF (9:1 , 100mL). To this solution at 0°C were added 1-hydroxybenzotriazole hydrate (1. ⁇ g, 11.1 mmol), water-soluble carbodiimide (1.3g, 6.8mmoI), piperidine (484mg, ⁇ .69mmol) and N-methylmorpholine (800mg, ⁇ mmol).
- N-2 x -(terf-Butyloxycarbonyl)-N-(2"-(9-fIuorenylmethyloxycarbonyl aminoethyl)-glycine (1.0g, 2.27mmoI) was dissolved in CH 2 CI 2 /DMF (9:1 , 10OmL).
- 1-hydroxybenzotriazole hydrate (620mg, 4.6mmol)
- water-soluble carbodiimide ⁇ 60mg, 2.8mmol
- 3,3-difluoropyrrolidine hydrochloride 360mg, 2. ⁇ mmol
- N-methylmorpholine ⁇ OOmg, ⁇ mmol
- Cyanuric chloride (1. ⁇ 44g, 10mmol) was dissolved in acetonitrile (20mL). The solution was cooled to -20 °C. A solution of 4-fluoroaniline (1.1g, 10mmol) and triethylamine (1.0g, 10mmol) was slowly added. After 1 hour at -20 °C the solvent was removed in vacuo and the residue was taken up in ethyl acetate (1 ⁇ 0mL). The solution was washed with water (1 x ⁇ OmL) and brine (1 x ⁇ OmL), dried (Na 2 S0 4 ) and evaporated in vacuo.
Abstract
Description
Claims
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002464254A CA2464254A1 (en) | 2001-10-23 | 2002-10-23 | Inhibitors of post-proline cleaving proteases |
HU0401738A HUP0401738A2 (en) | 2001-10-23 | 2002-10-23 | Inhibitors of post-proline cleaving proteases and pharmaceutical compositions containing them |
AU2002336190A AU2002336190B2 (en) | 2001-10-23 | 2002-10-23 | Inhibitors of Post-Proline Cleaving Proteases |
US10/491,794 US7335677B2 (en) | 2001-10-23 | 2002-10-23 | Inhibitors of dipeptidyl peptidase IV |
NZ532048A NZ532048A (en) | 2001-10-23 | 2002-10-23 | Inhibitors of post-proline cleaving proteases |
JP2003537624A JP2005511541A (en) | 2001-10-23 | 2002-10-23 | Inhibitors of post-proline cleavage protease |
IL16119102A IL161191A0 (en) | 2001-10-23 | 2002-10-23 | Inhibitors of post-proline cleaving proteases |
MXPA04003829A MXPA04003829A (en) | 2001-10-23 | 2002-10-23 | Inhibitors of dipeptidyl peptidase iv. |
KR10-2004-7005918A KR20040047943A (en) | 2001-10-23 | 2002-10-23 | Inhibitors of dipeptidyl peptidase iv |
EP02770089A EP1446116A1 (en) | 2001-10-23 | 2002-10-23 | Inhibitors of dipeptidyl peptidase iv |
NO20042080A NO20042080L (en) | 2001-10-23 | 2004-05-19 | Inhibitors of post-proline cleavage proteases |
US12/004,054 US20080255126A1 (en) | 2001-10-23 | 2007-12-20 | Inhibitors of post-proline cleaving proteases |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0125445.7A GB0125445D0 (en) | 2001-10-23 | 2001-10-23 | Protease Inhibitors |
GB0125445.7 | 2001-10-23 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US12/004,054 Division US20080255126A1 (en) | 2001-10-23 | 2007-12-20 | Inhibitors of post-proline cleaving proteases |
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WO2003035057A1 true WO2003035057A1 (en) | 2003-05-01 |
Family
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Family Applications (1)
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PCT/GB2002/004764 WO2003035057A1 (en) | 2001-10-23 | 2002-10-23 | Inhibitors of dipeptidyl peptidase iv |
Country Status (17)
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US (2) | US7335677B2 (en) |
EP (1) | EP1446116A1 (en) |
JP (1) | JP2005511541A (en) |
KR (1) | KR20040047943A (en) |
CN (1) | CN1571667A (en) |
AU (1) | AU2002336190B2 (en) |
CA (1) | CA2464254A1 (en) |
GB (1) | GB0125445D0 (en) |
HU (1) | HUP0401738A2 (en) |
IL (1) | IL161191A0 (en) |
MX (1) | MXPA04003829A (en) |
NO (1) | NO20042080L (en) |
NZ (1) | NZ532048A (en) |
PL (1) | PL370220A1 (en) |
RU (1) | RU2345065C2 (en) |
WO (1) | WO2003035057A1 (en) |
ZA (1) | ZA200402501B (en) |
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- 2001-10-23 GB GBGB0125445.7A patent/GB0125445D0/en not_active Ceased
-
2002
- 2002-10-23 EP EP02770089A patent/EP1446116A1/en not_active Withdrawn
- 2002-10-23 AU AU2002336190A patent/AU2002336190B2/en not_active Ceased
- 2002-10-23 HU HU0401738A patent/HUP0401738A2/en unknown
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Also Published As
Publication number | Publication date |
---|---|
RU2004110719A (en) | 2005-10-20 |
PL370220A1 (en) | 2005-05-16 |
JP2005511541A (en) | 2005-04-28 |
ZA200402501B (en) | 2005-01-13 |
CN1571667A (en) | 2005-01-26 |
NZ532048A (en) | 2004-10-29 |
US20050043299A1 (en) | 2005-02-24 |
EP1446116A1 (en) | 2004-08-18 |
RU2345065C2 (en) | 2009-01-27 |
AU2002336190B2 (en) | 2006-11-30 |
NO20042080L (en) | 2004-07-16 |
CA2464254A1 (en) | 2003-05-01 |
US7335677B2 (en) | 2008-02-26 |
GB0125445D0 (en) | 2001-12-12 |
HUP0401738A2 (en) | 2004-12-28 |
US20080255126A1 (en) | 2008-10-16 |
KR20040047943A (en) | 2004-06-05 |
MXPA04003829A (en) | 2004-07-16 |
IL161191A0 (en) | 2004-08-31 |
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