SK134498A3 - Novel 'alpha'-hydroxylic acid derivatives, their production and use - Google Patents
Novel 'alpha'-hydroxylic acid derivatives, their production and use Download PDFInfo
- Publication number
- SK134498A3 SK134498A3 SK1344-98A SK134498A SK134498A3 SK 134498 A3 SK134498 A3 SK 134498A3 SK 134498 A SK134498 A SK 134498A SK 134498 A3 SK134498 A3 SK 134498A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- phenyl
- alkoxy
- alkylthio
- amino
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000003814 drug Substances 0.000 claims abstract description 3
- -1 mercapto, amino Chemical group 0.000 claims description 138
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000001118 alkylidene group Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 150000002825 nitriles Chemical group 0.000 claims description 7
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 5
- 102000010180 Endothelin receptor Human genes 0.000 claims description 5
- 108050001739 Endothelin receptor Proteins 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 208000009304 Acute Kidney Injury Diseases 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 201000006474 Brain Ischemia Diseases 0.000 claims description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 2
- 206010019280 Heart failures Diseases 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 208000033626 Renal failure acute Diseases 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 201000011040 acute kidney failure Diseases 0.000 claims description 2
- 208000012998 acute renal failure Diseases 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 238000002399 angioplasty Methods 0.000 claims description 2
- 230000003042 antagnostic effect Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 206010008118 cerebral infarction Diseases 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 230000036454 renin-angiotensin system Effects 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 8
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000020832 chronic kidney disease Diseases 0.000 claims 1
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 51
- 239000000203 mixture Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 17
- 102000002045 Endothelin Human genes 0.000 description 16
- 108050009340 Endothelin Proteins 0.000 description 16
- 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 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
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- 239000000243 solution Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 101800004490 Endothelin-1 Proteins 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- 102000005962 receptors Human genes 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
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- 229960005181 morphine Drugs 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
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- 230000027455 binding Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- RJUDROONFFKPJA-UHFFFAOYSA-N 2-hydroxy-3,3-diphenylbutanenitrile Chemical compound C=1C=CC=CC=1C(C(O)C#N)(C)C1=CC=CC=C1 RJUDROONFFKPJA-UHFFFAOYSA-N 0.000 description 5
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- 239000008346 aqueous phase Substances 0.000 description 5
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 5
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- XQYZCPRMUQDJTD-UHFFFAOYSA-N ethyl 2-hydroxy-3,3-diphenylbutanoate Chemical compound C=1C=CC=CC=1C(C)(C(O)C(=O)OCC)C1=CC=CC=C1 XQYZCPRMUQDJTD-UHFFFAOYSA-N 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
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- 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 3
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 description 2
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Classifications
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- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
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- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
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- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
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- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19614533A DE19614533A1 (de) | 1996-04-12 | 1996-04-12 | Neue alpha-Hydroxysäurederivate, ihre Herstellung und Verwendung |
PCT/EP1997/001688 WO1997038981A1 (de) | 1996-04-12 | 1997-04-04 | NEUE α-HYDROXYSÄUREDERIVATE, IHRE HERSTELLUNG UND VERWENDUNG |
Publications (1)
Publication Number | Publication Date |
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SK134498A3 true SK134498A3 (en) | 1999-03-12 |
Family
ID=7791117
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK1344-98A SK134498A3 (en) | 1996-04-12 | 1997-04-04 | Novel 'alpha'-hydroxylic acid derivatives, their production and use |
Country Status (25)
Country | Link |
---|---|
US (1) | US6686369B1 (xx) |
EP (1) | EP0892787B1 (xx) |
JP (1) | JP2000508326A (xx) |
KR (1) | KR20000005369A (xx) |
AR (1) | AR007767A1 (xx) |
AT (1) | ATE242770T1 (xx) |
AU (1) | AU731579B2 (xx) |
BG (1) | BG102868A (xx) |
BR (1) | BR9708608A (xx) |
CA (1) | CA2250757A1 (xx) |
CO (1) | CO4900040A1 (xx) |
DE (2) | DE19614533A1 (xx) |
HR (1) | HRP970198A2 (xx) |
HU (1) | HUP9901312A3 (xx) |
ID (1) | ID16501A (xx) |
IL (1) | IL126350A0 (xx) |
NO (1) | NO311801B1 (xx) |
NZ (1) | NZ332096A (xx) |
PL (1) | PL329241A1 (xx) |
SK (1) | SK134498A3 (xx) |
TR (1) | TR199802039T2 (xx) |
TW (1) | TW425383B (xx) |
UA (1) | UA49884C2 (xx) |
WO (1) | WO1997038981A1 (xx) |
ZA (1) | ZA973097B (xx) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0946524A1 (de) * | 1996-12-18 | 1999-10-06 | Basf Aktiengesellschaft | Heterozyklische carbonsäurederivate, ihre herstellung und verwendung als endothelinrezeptorantagonisten |
US6030975A (en) * | 1997-03-14 | 2000-02-29 | Basf Aktiengesellschaft | Carboxylic acid derivatives, their preparation and use in treating cancer |
DE19726146A1 (de) * | 1997-06-19 | 1998-12-24 | Basf Ag | Neue ß-Amino und ß-Azidopcarbonsäurederivate, ihre Herstellung und Verwendung als Endothelinrezeptorantagonisten |
JP2002507996A (ja) * | 1997-07-03 | 2002-03-12 | デュポン ファーマシューティカルズ カンパニー | 神経学的障害を治療するためのイミダゾピリミジン類およびイミダゾピリジン類 |
DE19743681A1 (de) * | 1997-10-02 | 1999-04-08 | Knoll Ag | Methode zur Verhinderung der Transplantatabstoßung |
JP5187991B2 (ja) | 1997-10-17 | 2013-04-24 | アーク・セラピューティックス・リミテッド | レニン−アンジオテンシン系の阻害剤の使用 |
DE19806438A1 (de) * | 1998-02-17 | 1999-08-19 | Basf Ag | Neue Carbonsäurederivate mit 5-substituiertem Pyrimidinring, ihre Herstellung und Verwendung |
US6124463A (en) * | 1998-07-02 | 2000-09-26 | Dupont Pharmaceuticals | Benzimidazoles as corticotropin release factor antagonists |
US6365589B1 (en) | 1998-07-02 | 2002-04-02 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
US7566452B1 (en) | 1999-05-04 | 2009-07-28 | New York University | Cancer treatment with endothelin receptor antagonists |
DE10064797A1 (de) * | 2000-12-22 | 2002-06-27 | Knoll Ag | Orale und parenterale pharmazeutische Formulierung, umfassend eine niedermolekulare Thrombininhibitor-Pro-Pharmakon |
EP1243262B1 (en) | 2001-03-20 | 2006-05-31 | Schwarz Pharma Ag | Novel use of a peptide class of compound for treating non-neuropathic inflammatory pain |
EP1243263B1 (en) | 2001-03-21 | 2002-11-27 | Schwarz Pharma Ag | Novel use of a peptide class of compound for treating allodynia or other different types of chronic or phantom pain |
MXPA06011937A (es) | 2004-04-16 | 2007-01-26 | Sanol Arznei Schwarz Gmbh | Uso de compuestos peptidicos para la profilaxis y el tratamiento de dolor de cabeza cronico. |
EP1604656A1 (en) | 2004-06-09 | 2005-12-14 | Schwarz Pharma Ag | Novel use of peptide compounds for treating amyotrophic lateral sclerosis (ALS) |
BRPI0514721A (pt) | 2004-08-27 | 2008-06-24 | Sanol Arznei Schwarz Gmbh | uso de compostos de peptìdeos para tratar dor de cáncer ósseo, dor induzida por quimioterapia e nucleosìdeo |
KR20080111137A (ko) * | 2006-04-13 | 2008-12-22 | 액테리온 파마슈티칼 리미티드 | 초기 단계 특발성 폐 섬유증을 위한 엔도텔린 수용체 대항제 |
SI2462990T1 (sl) | 2006-06-15 | 2014-04-30 | Ucb Pharma Gmbh | Farmacevtski sestavek, ki obsega lakozamid in levetiracetam, s sinergističnim antikonvulzivnim učinkom |
WO2011022694A2 (en) * | 2009-08-20 | 2011-02-24 | University Of Tennessee Research Foundation, The | Furanopyrimidine cannabinoid compounds and related methods of use |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4035758A1 (de) * | 1990-11-08 | 1992-05-14 | Schering Ag | Substituierte (alpha)-pyrimidinyloxy(thio)- und (alpha)-triazinyloxy(thio)-carbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, fungizider und pflanzenwachstumsregulierender wirkung |
DE4313412A1 (de) | 1993-04-23 | 1994-10-27 | Basf Ag | 3-(Het)aryl-Carbonsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung |
DE4411225A1 (de) | 1994-03-31 | 1995-10-05 | Basf Ag | Verwendung von Carbonsäurederivaten als Arzneimittel |
DE19533023B4 (de) * | 1994-10-14 | 2007-05-16 | Basf Ag | Neue Carbonsäurederivate, ihre Herstellung und Verwendung |
-
1996
- 1996-04-12 DE DE19614533A patent/DE19614533A1/de not_active Withdrawn
-
1997
- 1997-04-04 NZ NZ332096A patent/NZ332096A/xx unknown
- 1997-04-04 KR KR1019980708091A patent/KR20000005369A/ko not_active Application Discontinuation
- 1997-04-04 HU HU9901312A patent/HUP9901312A3/hu unknown
- 1997-04-04 US US09/155,944 patent/US6686369B1/en not_active Expired - Fee Related
- 1997-04-04 EP EP97918110A patent/EP0892787B1/de not_active Expired - Lifetime
- 1997-04-04 IL IL12635097A patent/IL126350A0/xx unknown
- 1997-04-04 WO PCT/EP1997/001688 patent/WO1997038981A1/de not_active Application Discontinuation
- 1997-04-04 UA UA98116020A patent/UA49884C2/uk unknown
- 1997-04-04 AU AU26365/97A patent/AU731579B2/en not_active Ceased
- 1997-04-04 BR BR9708608A patent/BR9708608A/pt not_active IP Right Cessation
- 1997-04-04 PL PL97329241A patent/PL329241A1/xx unknown
- 1997-04-04 CA CA002250757A patent/CA2250757A1/en not_active Abandoned
- 1997-04-04 JP JP9536699A patent/JP2000508326A/ja active Pending
- 1997-04-04 TR TR1998/02039T patent/TR199802039T2/xx unknown
- 1997-04-04 AT AT97918110T patent/ATE242770T1/de not_active IP Right Cessation
- 1997-04-04 SK SK1344-98A patent/SK134498A3/sk unknown
- 1997-04-04 DE DE59710272T patent/DE59710272D1/de not_active Expired - Fee Related
- 1997-04-11 CO CO97018892A patent/CO4900040A1/es unknown
- 1997-04-11 HR HR19614533.3A patent/HRP970198A2/xx not_active Application Discontinuation
- 1997-04-11 ZA ZA973097A patent/ZA973097B/xx unknown
- 1997-04-11 AR ARP970101460A patent/AR007767A1/es not_active Application Discontinuation
- 1997-04-12 TW TW086104727A patent/TW425383B/zh not_active IP Right Cessation
- 1997-04-14 ID IDP971242A patent/ID16501A/id unknown
-
1998
- 1998-10-09 NO NO19984717A patent/NO311801B1/no not_active IP Right Cessation
- 1998-10-26 BG BG102868A patent/BG102868A/bg unknown
Also Published As
Publication number | Publication date |
---|---|
AU2636597A (en) | 1997-11-07 |
BG102868A (bg) | 1999-11-30 |
EP0892787A1 (de) | 1999-01-27 |
NO984717L (no) | 1998-10-09 |
ID16501A (id) | 1997-10-02 |
DE19614533A1 (de) | 1997-10-16 |
AR007767A1 (es) | 1999-11-24 |
DE59710272D1 (de) | 2003-07-17 |
CA2250757A1 (en) | 1997-10-23 |
IL126350A0 (en) | 1999-05-09 |
BR9708608A (pt) | 1999-08-03 |
TR199802039T2 (xx) | 1999-01-18 |
HRP970198A2 (en) | 1998-04-30 |
NO984717D0 (no) | 1998-10-09 |
NO311801B1 (no) | 2002-01-28 |
AU731579B2 (en) | 2001-04-05 |
US6686369B1 (en) | 2004-02-03 |
HUP9901312A3 (en) | 2000-06-28 |
NZ332096A (en) | 2000-01-28 |
ATE242770T1 (de) | 2003-06-15 |
PL329241A1 (en) | 1999-03-15 |
UA49884C2 (uk) | 2002-10-15 |
TW425383B (en) | 2001-03-11 |
CO4900040A1 (es) | 2000-03-27 |
ZA973097B (en) | 1998-10-12 |
JP2000508326A (ja) | 2000-07-04 |
KR20000005369A (ko) | 2000-01-25 |
EP0892787B1 (de) | 2003-06-11 |
HUP9901312A2 (hu) | 1999-08-30 |
WO1997038981A1 (de) | 1997-10-23 |
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