RU96121599A - 3-N-ACYLAMINOPYRIDINE DERIVATIVES AND METHOD FOR THEIR PRODUCTION - Google Patents
3-N-ACYLAMINOPYRIDINE DERIVATIVES AND METHOD FOR THEIR PRODUCTIONInfo
- Publication number
- RU96121599A RU96121599A RU96121599/04A RU96121599A RU96121599A RU 96121599 A RU96121599 A RU 96121599A RU 96121599/04 A RU96121599/04 A RU 96121599/04A RU 96121599 A RU96121599 A RU 96121599A RU 96121599 A RU96121599 A RU 96121599A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- substituted
- hydrogen
- benzyl
- halogen
- Prior art date
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- -1 oxetane-3-yl Chemical group 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 229940090121 Sulfonylureas for blood glucose lowering Drugs 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 1
- 0 CC(C=C1)C=CC(S**)=C1N(*)C(C1*)C1=O Chemical compound CC(C=C1)C=CC(S**)=C1N(*)C(C1*)C1=O 0.000 description 1
Claims (3)
где R1 обозначает водород, галоген, С1-С4-алкил, С1-С4-алкокси или С1-С4-алкилтио, или одно- либо многократно замещенный галогеном С1-С4-алкил;
R2 - водород, С1-С6-алкил или С1-С6-алкил, одно- либо многократно замещенный галогеном, С1-С6-алкокси, С3-С6-алкенилокси, С3-С6-алкинилокси или же С1-С6-алкилтио;
R3 - водород, С1-С6-алкил, С3-С6-циклоалкил, С2-С6-алкинил; или С1-С6-алкил либо С3-С6-циклоалкил, замещенные галогеном, либо С1-С4-алкокси; С2-С6-алкенил либо С2-С6-алкенил, замещенный галогеном; фенил, бензил, нафтил или ОR3 1 или фенил, бензил, нафтил, замещенные галогеном, С1-С4-алкилом, С1-С4-галогеналкилом, С1-С4-алкокси, С1-С4-галогеналкокси,
С3-С6-алкенилокси, С3-С6-алкинилокси, нитро, циано, COOR5, NR6R7, C(O)NR8R9, X1R10, SO2NR11R12 или X2R13, R3 1 обозначает С1-С6-алкил,
С1-С6-галогеналкил, оксетан-3-ил, С4-С6-циклоалкил, который может быть замещен галогеном, С1-С4- алкилом либо С1-С4-алкокси; фенил, бензил, нафтил или фенил, бензил, нафтил, замещенные С1-С4-алкилом, С1-С4-галогеналкилом, С1-С4-алкокси, С1-С4-галогеналкокси, С1-С4-алкилтио, С1-С4-галогеналкилтио, С1-С4-алкилсульфонилом, С1-С4-алкилсульфинилом, нитро, циано, COOR16, NR17R18, CONR19R20 или же SO2NR21R22; С1-С6-алкил, замещенный С1-С4-алкокси, С3-С6-циклоалкилом, циано, COOR23 либо CONR24R25; С3-С6-алкенил, С3-С6-галогеналкенил, С3-С6-алкинил, С3-С6-галогеналкинил, X3R26 или же X4R27; R5 - водород, С1-С6-алкил, С3-С6-алкенил -C3-C6-алкинил или оксетан-3-ил; R22, R6, R7, R8, R9, R11, R12, R17, R18, R19, R20, R21, R24 и R25 обозначают независимо друг от друга водород, С1-С4-алкил, С3-С6-алкенил или С3-С6-алкинил или R6 представляет собой группу -С(О)-Х5-С1-С4-алкил либо -С(О)-С1-С4-алкил, которые могут быть замещены галогеном, или R6 и R7, либо R8 и R9, либо R11 и R12, либо R17 и R18, либо R19 и R20, либо R21 и R22, либо R24 и R25 вместе представляют собой С4-С5-алкиленовую цепь, которая может быть прервана кислородом или NR14; R14 - водород, С1-С4-алкил, C3-C6-алкенил или С3-С6-алкинил; R10 и R26 обозначают независимо друг от друга С1-С4-алкил или С1-С4-галогеналкил; R13 - С1-С4-алкил, замещенный СООR15; R23, R16, R15 - водород или С1-С4-алкил; Х5 - кислород или NR28 и R28 - водород, С1-С4-алкил, С3-C6-алкенил или С3-С6-алкинил;
R4 - бензил, метоксибензил, изопропил.1. Derivatives of 3-N-acylaminopyridine General formula I
where R 1 denotes hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio, or mono- or multiply substituted by halogen C 1 -C 4 -alkyl;
R 2 is hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkyl, once or repeatedly substituted by halogen, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 - alkynyloxy or C 1 -C 6 -alkylthio;
R 3 is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkynyl; or C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl, substituted with halogen, or C 1 -C 4 -alkoxy; C 2 -C 6 alkenyl or C 2 -C 6 alkenyl substituted with halogen; phenyl, benzyl, naphthyl or OR 3 1 or phenyl, benzyl, naphthyl, substituted with halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy ,
C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, nitro, cyano, COOR 5 , NR 6 R 7 , C (O) NR 8 R 9 , X 1 R 10 , SO 2 NR 11 R 12 or X 2 R 13 , R 3 1 stands for C 1 -C 6 -alkyl,
C 1 -C 6 haloalkyl, oxetan-3-yl, C 4 -C 6 -cycloalkyl which may be substituted by halogen, C 1 -C 4 - alkyl or C 1 -C 4 -alkoxy; phenyl, benzyl, naphthyl or phenyl, benzyl, naphthyl, substituted with C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -halogenoalkylthio, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkylsulfinyl, nitro, cyano, COOR 16 , NR 17 R 18 , CONR 19 R 20 or SO 2 NR 21 R 22 ; C 1 -C 6 alkyl substituted with C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl, cyano, COOR 23 or CONR 24 R 25 ; C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, X 3 R 26 or X 4 R 27 ; R 5 - hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 alkenyl -C 3 -C 6 -alkynyl or oxetane-3-yl; R 22 , R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , R 17 , R 18 , R 19 , R 20 , R 21 , R 24 and R 25 denote independently of each other hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, or R 6 is a group -C (O) -X 5 -C 1 -C 4 -alkyl or -C (O) - C 1 -C 4 -alkyl, which may be substituted by halogen, or R 6 and R 7 , or R 8 and R 9 , or R 11 and R 12 , or R 17 and R 18 , or R 19 and R 20 , or R 21 and R 22 , or R 24 and R 25 together represent a C 4 -C 5 alkylene chain which can be interrupted by oxygen or NR 14 ; R 14 is hydrogen, C 1 -C 4 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl; R 10 and R 26 are independently of each other C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; R 13 is C 1 -C 4 -alkyl substituted with COOR 15 ; R 23 , R 16 , R 15 is hydrogen or C 1 -C 4 -alkyl; X 5 is oxygen or NR 28 and R 28 is hydrogen, C 1 -C 4 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;
R 4 - benzyl, methoxybenzyl, isopropyl.
где R1, R2 и R3 имеют значения, указанные в п.1;
R4 - бензил, метоксиметил или изопропил по п.1,
в качестве промежуточных продуктов для получения сульфонилмочевины формулы
где R1, R2 и R3 имеют значение, указанное в п.1;
R'4 - водород или метил;
R'2 - метил или метокси.2. Derivatives of 3-N-acylaminopyridine of General Formula I
where R 1 , R 2 and R 3 have the meanings indicated in paragraph 1;
R 4 is benzyl, methoxymethyl or isopropyl according to claim 1,
as intermediate products for the production of sulfonylureas of the formula
where R 1 , R 2 and R 3 have the meaning given in claim 1;
R ' 4 is hydrogen or methyl;
R ' 2 is methyl or methoxy.
где R1, R2 и R3 имеют значения, указанные в п.1;
R4 - бензил, метоксиметил или изопропил;
отличающийся тем, что осуществляют реакцию между соединением формулы II
где R1 и R2 имеют значения, указанные в п.1;
R4 - бензил, метоксиметил или изопропил,
и соединением формулы III
Z - R5,
где R5 представляет собой группу С(О)-R3;
R3 имеет значение, указанное в п.1; Z обозначает отщепляемую группу,
в присутствии основания.3. The method of obtaining derivatives of 3-N-acylaminopyridine General formula I
where R 1 , R 2 and R 3 have the meanings indicated in paragraph 1;
R 4 is benzyl, methoxymethyl or isopropyl;
characterized in that they carry out the reaction between the compound of formula II
where R 1 and R 2 have the meanings indicated in claim 1;
R 4 is benzyl, methoxymethyl or isopropyl,
and a compound of formula III
Z - R 5 ,
where R 5 represents the group C (O) -R 3 ;
R 3 has the meaning given in claim 1; Z denotes a leaving group,
in the presence of a base.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3697/92-2 | 1992-12-02 | ||
| CH213/93-1 | 1993-01-25 | ||
| CH397/93-4 | 1993-02-10 | ||
| CH906/93-0 | 1993-03-25 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU93053027/04A Division RU93053027A (en) | 1992-12-02 | 1993-11-30 | SELECTIVE HERBICIDAL PRODUCT |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU96121599A true RU96121599A (en) | 1999-02-20 |
Family
ID=
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2451512C2 (en) * | 2006-02-07 | 2012-05-27 | Мицубиси Танабе Фарма Корпорейшн | Neurogenesis mediated with 4-acylaminopyridine derivatives |
| RU2463303C2 (en) * | 2005-11-08 | 2012-10-10 | Вертекс Фармасьютикалз Инкорпорейтед | Heterocyclic modulators of atp-binding cartridge transporter |
| US9725440B2 (en) | 2007-05-09 | 2017-08-08 | Vertex Pharmaceuticals Incorporated | Modulators of CFTR |
| US9751890B2 (en) | 2008-02-28 | 2017-09-05 | Vertex Pharmaceuticals Incorporated | Heteroaryl derivatives as CFTR modulators |
| US9776968B2 (en) | 2007-12-07 | 2017-10-03 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxamido-pyridine benzoic acids |
| US9840499B2 (en) | 2007-12-07 | 2017-12-12 | Vertex Pharmaceuticals Incorporated | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid |
| US10076513B2 (en) | 2010-04-07 | 2018-09-18 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of 3-(6-(1-(2,2-difluorobenzo[D][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid and administration thereof |
| US10231932B2 (en) | 2013-11-12 | 2019-03-19 | Vertex Pharmaceuticals Incorporated | Process of preparing pharmaceutical compositions for the treatment of CFTR mediated diseases |
| US10302602B2 (en) | 2014-11-18 | 2019-05-28 | Vertex Pharmaceuticals Incorporated | Process of conducting high throughput testing high performance liquid chromatography |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10626111B2 (en) | 2004-01-30 | 2020-04-21 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| RU2463303C2 (en) * | 2005-11-08 | 2012-10-10 | Вертекс Фармасьютикалз Инкорпорейтед | Heterocyclic modulators of atp-binding cartridge transporter |
| RU2608610C2 (en) * | 2005-11-08 | 2017-01-23 | Вертекс Фармасьютикалз Инкорпорейтед | Heterocyclic modulators of atp-binding cassette transporters |
| US11084804B2 (en) | 2005-11-08 | 2021-08-10 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| RU2451512C2 (en) * | 2006-02-07 | 2012-05-27 | Мицубиси Танабе Фарма Корпорейшн | Neurogenesis mediated with 4-acylaminopyridine derivatives |
| US9725440B2 (en) | 2007-05-09 | 2017-08-08 | Vertex Pharmaceuticals Incorporated | Modulators of CFTR |
| US9840499B2 (en) | 2007-12-07 | 2017-12-12 | Vertex Pharmaceuticals Incorporated | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid |
| US10597384B2 (en) | 2007-12-07 | 2020-03-24 | Vertex Pharmaceuticals Incorporated | Solid forms of 3-(6-(1-(2,2-difluorobenzo[D][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid |
| US9776968B2 (en) | 2007-12-07 | 2017-10-03 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxamido-pyridine benzoic acids |
| US9751890B2 (en) | 2008-02-28 | 2017-09-05 | Vertex Pharmaceuticals Incorporated | Heteroaryl derivatives as CFTR modulators |
| US10076513B2 (en) | 2010-04-07 | 2018-09-18 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of 3-(6-(1-(2,2-difluorobenzo[D][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid and administration thereof |
| US11052075B2 (en) | 2010-04-07 | 2021-07-06 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid and administration thereof |
| US10231932B2 (en) | 2013-11-12 | 2019-03-19 | Vertex Pharmaceuticals Incorporated | Process of preparing pharmaceutical compositions for the treatment of CFTR mediated diseases |
| US10302602B2 (en) | 2014-11-18 | 2019-05-28 | Vertex Pharmaceuticals Incorporated | Process of conducting high throughput testing high performance liquid chromatography |
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