HUP9901580A2 - Benzo-1,3-dioxolyl- and bezofuranyl substituted pyrrolidine derivatives as endothelin antagonists, process for their preparation and pharmaceutical compositions containing the same - Google Patents
Benzo-1,3-dioxolyl- and bezofuranyl substituted pyrrolidine derivatives as endothelin antagonists, process for their preparation and pharmaceutical compositions containing the sameInfo
- Publication number
- HUP9901580A2 HUP9901580A2 HU9901580A HUP9901580A HUP9901580A2 HU P9901580 A2 HUP9901580 A2 HU P9901580A2 HU 9901580 A HU9901580 A HU 9901580A HU P9901580 A HUP9901580 A HU P9901580A HU P9901580 A2 HUP9901580 A2 HU P9901580A2
- Authority
- HU
- Hungary
- Prior art keywords
- alkylene
- alkyl
- lower alkyl
- alkenyl
- haloalkyl
- Prior art date
Links
- 150000003235 pyrrolidines Chemical class 0.000 title abstract 2
- 102000002045 Endothelin Human genes 0.000 title 1
- 108050009340 Endothelin Proteins 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 18
- 125000002947 alkylene group Chemical group 0.000 abstract 10
- 125000003342 alkenyl group Chemical group 0.000 abstract 9
- 125000001188 haloalkyl group Chemical group 0.000 abstract 9
- 125000003118 aryl group Chemical group 0.000 abstract 8
- 125000000623 heterocyclic group Chemical group 0.000 abstract 8
- 125000004450 alkenylene group Chemical group 0.000 abstract 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 7
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 7
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 6
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 abstract 6
- 125000000304 alkynyl group Chemical group 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- JVWVTPZZEHLARL-OFEZKSIWSA-N (2r,3r,4s)-4-(1,3-benzodioxol-5-yl)-2-(3-fluoro-4-methoxyphenyl)-1-[2-[pentylsulfonyl(propyl)amino]ethyl]pyrrolidine-3-carboxylic acid Chemical compound C1([C@H]2[C@@H]([C@H](CN2CCN(CCC)S(=O)(=O)CCCCC)C=2C=C3OCOC3=CC=2)C(O)=O)=CC=C(OC)C(F)=C1 JVWVTPZZEHLARL-OFEZKSIWSA-N 0.000 abstract 1
- 241000295146 Gallionellaceae Species 0.000 abstract 1
- 229910018828 PO3H2 Inorganic materials 0.000 abstract 1
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 abstract 1
- 102220008337 rs1437698471 Human genes 0.000 abstract 1
- 102220101549 rs199890548 Human genes 0.000 abstract 1
- 102220024172 rs397515479 Human genes 0.000 abstract 1
- 102220015875 rs6734111 Human genes 0.000 abstract 1
- 102220099820 rs878853791 Human genes 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- -1 sulphonamido Chemical group 0.000 abstract 1
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Pyrrolidine derivatives of formula (I) and their salts are new. Z = C(R18)(R19) or CO; R18, R19 = H or alkyl; n = 0 or 1; R = (CH2)mW; m = 0-6; W = CO2G, PO3H2, P(O)(OH)E, CN, CONHR17, alkylaminocarbonyl, dialkylaminocarbonyl, tetrazolyl, OH, alkoxy, sulphonamido, CONHSO2R16, SO2NHCOR16 or a e.g. group of formula (n)-(p); G =H or carboxy-protecting group; E =H, lower alkyl or arylalkyl; R17= lower alkyl; R16 = lower alkyl, haloalkyl, aryl or dialkylamino; R1= lower alkyl, alkenyl, haloalkyl, haloalkoxyalkyl, cycloalkylalkyl, aralkyl, aryloxyalkyl, arylalkoxyalkyl, (N-alkanoyl-N-alkyl)aminoalkyl, alkylsulphonylamidoalkyl or (heterocyclyl)alkyl; R5a = alkylene or alkenylene; R7 = bond, alkylene, alkenylene, N(R21)-R10 or R10a-N(R21)-R10; R10, R10a = alkylene or alkenylene; R21=H, lower alkyl, alkenyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, aryl or aralkyl; R4, R6 = e.g. (R11)(R12)N, lower alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, etc; z = 0-5; R11, R12 = H, lower alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclyl, aralkyl, (heterocyclyl)alkyl, hydroxyalkyl, alkoxy, aminoalkyl or trialkylaminoalkyl; R2 = e.g. H, lower alkyl, alkenyl, alkynyl, alkoxyalkyl, alkoxycarbonyl, hydroxyalkyl, haloalkyl or haloalkoxyalkyl, etc, provided that \- 1 of R1 and R2 is not H; R3 = R4COR5, R4R5a, R6SO2R7, R26SOR27, R22OCOR23, lower alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, aryloxyalkyl, heterocyclyl, (heterocyclyl)alkyl, alkoxyalkyl, alkoxyalkoxyalkyl or R13COCH(R14) or H, R5b-Q or R5b-NHR20 when Z = C(R18)(R19) and R18, R19 = H; R5 = bond, alkylene, alkenylene, N(R20)R8, R8a-N(R20)-R8, O-R9 or R9a-O-R9; R8, R8a = alkylene or alkenylene; R20 = H, lower alkyl, alkenyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkyl or cycloalkylalkyl; R9, R9a = alkylene; R26 = lower alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heterocyclyl, (heterocyclyl)alkyl, alkoxyalkyl or alkoxy substituted haloalkyl; R27= alkylene or alkenylene; R22 = carboxy protecting group or heterocyclyl; R23 = bond, alkylene, alkenylene or N(R24)-R25; R25= alkylene; R24 = H or alkyl; R13 = amino, alkylamino or dialkylamino; R14= aryl or R15CO; R15 = amino, alkylamino or dialkylamino; R5b = alkylene; Q = leaving group; R20a= H, alkyl, alkenyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl. 44 Compounds (I) are specifically claimed, e.g (2R,3R,4S)-2-(3-fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-1- (2-(N-propyl-N-pentanesulphonylamino)ethyl)-pyrrolidine-3-carboxylic acid.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60062596A | 1996-02-13 | 1996-02-13 | |
| US79450697A | 1997-02-04 | 1997-02-04 | |
| PCT/US1997/001936 WO1997030045A1 (en) | 1996-02-13 | 1997-02-12 | Novel benzo-1,3-dioxolyl- and benzofuranyl substituted pyrrolidine derivatives as endothelin antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP9901580A2 true HUP9901580A2 (en) | 2000-09-28 |
| HUP9901580A3 HUP9901580A3 (en) | 2000-10-30 |
| HU226888B1 HU226888B1 (en) | 2010-01-28 |
Family
ID=25162823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9901580A HU226888B1 (en) | 1996-02-13 | 1997-02-12 | Use of pyrrolidine derivatives for producing a medicament for the treatment of bone pain associated with bone cancer |
Country Status (2)
| Country | Link |
|---|---|
| HU (1) | HU226888B1 (en) |
| TW (1) | TW581760B (en) |
-
1997
- 1997-02-12 HU HU9901580A patent/HU226888B1/en not_active IP Right Cessation
- 1997-03-24 TW TW086103710A patent/TW581760B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9901580A3 (en) | 2000-10-30 |
| TW581760B (en) | 2004-04-01 |
| HU226888B1 (en) | 2010-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Lapse of definitive patent protection due to non-payment of fees |