CA2211889C - 2,3-dihydro-1,4-dioxynopyridines substitues a effet vasoconstricteur - Google Patents
2,3-dihydro-1,4-dioxynopyridines substitues a effet vasoconstricteur Download PDFInfo
- Publication number
- CA2211889C CA2211889C CA002211889A CA2211889A CA2211889C CA 2211889 C CA2211889 C CA 2211889C CA 002211889 A CA002211889 A CA 002211889A CA 2211889 A CA2211889 A CA 2211889A CA 2211889 C CA2211889 C CA 2211889C
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- Prior art keywords
- 6alkyl
- hydrogen
- amino
- formula
- mono
- Prior art date
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- QWQZJEXJTYAPGE-UHFFFAOYSA-N 2,3-dihydro-[1,4]dioxino[2,3-b]pyridine Chemical class C1=CC=C2OCCOC2=N1 QWQZJEXJTYAPGE-UHFFFAOYSA-N 0.000 title description 3
- 230000003639 vasoconstrictive effect Effects 0.000 title 1
- -1 cyano aminocarbonyl Chemical group 0.000 claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
- 239000001257 hydrogen Substances 0.000 claims abstract description 53
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 101100490437 Mus musculus Acvrl1 gene Chemical group 0.000 claims abstract 6
- 125000000815 N-oxide group Chemical group 0.000 claims abstract 2
- 150000002431 hydrogen Chemical group 0.000 claims description 31
- 150000003254 radicals Chemical class 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 125000003386 piperidinyl group Chemical group 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
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- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 12
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- MKWJJIHBKXTHIB-UHFFFAOYSA-N n'-(6-chloropyridazin-3-yl)-n'-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-2-ylmethyl)propane-1,3-diamine Chemical compound C1OC2=NC=CC=C2OC1CN(CCCN)C1=CC=C(Cl)N=N1 MKWJJIHBKXTHIB-UHFFFAOYSA-N 0.000 claims 1
- YMYQMABLLKTQML-UHFFFAOYSA-N n-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-2-ylmethyl)-n'-pyrimidin-2-ylpropane-1,3-diamine Chemical compound C1OC2=NC=CC=C2OC1CNCCCNC1=NC=CC=N1 YMYQMABLLKTQML-UHFFFAOYSA-N 0.000 claims 1
- JZGABJQCYNEJPM-UHFFFAOYSA-N n-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-ylmethyl)-n'-pyrimidin-2-ylpropane-1,3-diamine Chemical compound C1OC2=CC=CN=C2OC1CNCCCNC1=NC=CC=N1 JZGABJQCYNEJPM-UHFFFAOYSA-N 0.000 claims 1
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
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- FHYDQGOVTLQZSZ-UHFFFAOYSA-N n'-pyrimidin-2-ylpropane-1,3-diamine Chemical compound NCCCNC1=NC=CC=N1 FHYDQGOVTLQZSZ-UHFFFAOYSA-N 0.000 description 1
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- 239000002574 poison Substances 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention porte sur des composés de formule (I), sur leurs formes N-oxyde, sur leurs sels acides d'addition pharmacocompatibles et leurs formes stéréochimiquement isomériques. Dans ladite formule, =a1-a2=a3-a4= est un radical bivalent de formule (a) =N-CH=CH-CH= (b), =CH-N=CH-CH= (c), =CH-CH=N=CH (d), =CH-CH=CH-N-, dans laquelle un ou deux atomes d'hydrogène peuvent être substitués par halo, hydroxy, C1-6 alkyle ou C1-6 alkyloxy; R<1> est hydrogène ou C1-6 alkyle; R<2> est hydrogène ou C1-6 alkyle; R<3> est hydrogène ou C1-6 alkyle; Alk<1> est C1-5 alcanediyle; Alk<2> est C2-15 alcanediyle; Q est un anneau hétérocyclique à 5 ou 6 éléments contenant au moins un atome d'azote ou un radical de formule -C(NR5R6)=C-R4 dans laquelle R<4> est hydrogène, cyano, aminocarbonyle ou C1-6 alkyle; R<5> est hydrogène, C1-6 alkyle, C3-6 alcényle ou C3-6 alcynyle, R<6> est hydrogène ou C1-6 alkyle; et R<5> et R<6> pris ensemble peuvent former un radical bivalent de formule -(CH2)4- ou -(CH2)5-. Sont également présentées des compositions et préparations pharmaceutiques et leur utilisation comme médicaments.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95200290.5 | 1995-02-07 | ||
| EP95200290 | 1995-02-07 | ||
| PCT/EP1996/000396 WO1996024596A1 (fr) | 1995-02-07 | 1996-01-30 | 2,3-dihydro-1,4-dioxynopyridines substitues a effet vasoconstricteur |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2211889A1 CA2211889A1 (fr) | 1996-08-15 |
| CA2211889C true CA2211889C (fr) | 2006-10-10 |
Family
ID=37111755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002211889A Expired - Lifetime CA2211889C (fr) | 1995-02-07 | 1996-01-30 | 2,3-dihydro-1,4-dioxynopyridines substitues a effet vasoconstricteur |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2211889C (fr) |
-
1996
- 1996-01-30 CA CA002211889A patent/CA2211889C/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2211889A1 (fr) | 1996-08-15 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20160201 |