FI86431C - Foerfarande foer framstaellning av -d-ribofuranuronsyratioamider. - Google Patents
Foerfarande foer framstaellning av -d-ribofuranuronsyratioamider. Download PDFInfo
- Publication number
- FI86431C FI86431C FI875491A FI875491A FI86431C FI 86431 C FI86431 C FI 86431C FI 875491 A FI875491 A FI 875491A FI 875491 A FI875491 A FI 875491A FI 86431 C FI86431 C FI 86431C
- Authority
- FI
- Finland
- Prior art keywords
- purinyl
- deoxy
- ethylthioamide
- acid
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 25
- -1 6-amino-9-purinyl Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 150000003556 thioamides Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- QPIYPWGWBLCOPY-AVRIJYDRSA-N (2s,3s,4r,5r)-3,4,5-trihydroxyoxolane-2-carboxylic acid Chemical compound O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H]1O QPIYPWGWBLCOPY-AVRIJYDRSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 108050000203 Adenosine receptors Proteins 0.000 description 3
- 102000009346 Adenosine receptors Human genes 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 102100028255 Renin Human genes 0.000 description 3
- 108090000783 Renin Proteins 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- 229940030600 antihypertensive agent Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 210000005036 nerve Anatomy 0.000 description 3
- WDSFCZDGCAXRDY-UHFFFAOYSA-N s-ethylthiohydroxylamine Chemical compound CCSN WDSFCZDGCAXRDY-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000024883 vasodilation Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 101150007969 ADORA1 gene Proteins 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- BHMZHLVLASSMIX-UHFFFAOYSA-N COC1=CC=C(C=C1)S[PH2]=S Chemical class COC1=CC=C(C=C1)S[PH2]=S BHMZHLVLASSMIX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 150000003838 adenosines Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 210000003989 endothelium vascular Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 230000001435 haemodynamic effect Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000006194 pentinyl group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000003379 purinergic P1 receptor agonist Substances 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3642748 | 1986-12-15 | ||
| DE3642748 | 1986-12-15 | ||
| DE3729768 | 1987-09-05 | ||
| DE3729768 | 1987-09-05 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI875491A0 FI875491A0 (fi) | 1987-12-14 |
| FI875491L FI875491L (fi) | 1988-06-16 |
| FI86431B FI86431B (fi) | 1992-05-15 |
| FI86431C true FI86431C (fi) | 1992-08-25 |
Family
ID=25850352
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI875491A FI86431C (fi) | 1986-12-15 | 1987-12-14 | Foerfarande foer framstaellning av -d-ribofuranuronsyratioamider. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4855288A (enExample) |
| KR (1) | KR880007533A (enExample) |
| AT (1) | AT393506B (enExample) |
| AU (1) | AU601247B2 (enExample) |
| BE (1) | BE1001621A3 (enExample) |
| CA (1) | CA1291752C (enExample) |
| CH (1) | CH676851A5 (enExample) |
| DK (1) | DK655487A (enExample) |
| ES (1) | ES2010736A6 (enExample) |
| FI (1) | FI86431C (enExample) |
| FR (1) | FR2608159B1 (enExample) |
| GB (1) | GB2199036B (enExample) |
| GR (1) | GR871895B (enExample) |
| HU (1) | HU198950B (enExample) |
| IL (1) | IL84808A (enExample) |
| IT (1) | IT1230116B (enExample) |
| LU (1) | LU87071A1 (enExample) |
| MY (1) | MY102270A (enExample) |
| NL (1) | NL8702926A (enExample) |
| NZ (1) | NZ222897A (enExample) |
| PH (1) | PH25421A (enExample) |
| SE (1) | SE8704979L (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU87181A1 (fr) * | 1987-04-06 | 1988-11-17 | Sandoz Sa | Nouveaux derives de l'acide furannuronique,leur preparation et leur utilisation comme medicaments |
| US5219840A (en) * | 1987-04-06 | 1993-06-15 | Sandoz Ltd. | Antihypertensive 9-(2,N6 -disubstituted adenyl) ribofuranuronic acid derivatives |
| DK0550631T3 (da) * | 1990-09-25 | 1997-01-20 | Rhone Poulenc Rorer Int | Forbindelser med blodtrykssænkende virkning og virkning mod iskæmi |
| US5561134A (en) * | 1990-09-25 | 1996-10-01 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties |
| GB9111580D0 (en) * | 1991-05-30 | 1991-07-24 | Wellcome Found | Nucleoside derivative |
| FR2687678B1 (fr) * | 1992-01-31 | 1995-03-31 | Union Pharma Scient Appl | Nouveaux derives de l'adenosine, leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| TW528755B (en) | 1996-12-24 | 2003-04-21 | Glaxo Group Ltd | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
| YU44900A (sh) | 1998-01-31 | 2003-01-31 | Glaxo Group Limited | Derivati 2-(purin-9-il)tetrahidrofuran-3,4-diola |
| CN1313861A (zh) | 1998-06-23 | 2001-09-19 | 葛兰素集团有限公司 | 2－(嘌呤－9－基)－四氢呋喃－3,4－二醇衍生物 |
| AR049384A1 (es) | 2004-05-24 | 2006-07-26 | Glaxo Group Ltd | Derivados de purina |
| GB0514809D0 (en) * | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6717061A (enExample) * | 1966-12-21 | 1968-06-24 | ||
| US4029884A (en) * | 1971-03-18 | 1977-06-14 | Abbott Laboratories | Adenosine-5'-carboxylic acid amides |
| CA1082695A (en) * | 1972-04-10 | 1980-07-29 | Francis E. Fischer | Process for preparing adenosine-5'-carboxamides |
| US3966917A (en) * | 1974-07-30 | 1976-06-29 | Abbott Laboratories | Platelet aggregation inhibitors |
| DE2610985A1 (de) * | 1976-03-16 | 1977-09-29 | Byk Gulden Lomberg Chem Fab | Arzneimittel enthaltend beta-d-1 (6-amino-9h-purin-9-yl)-1-deoxyribofuranuronsaeurederivate |
| LU75374A1 (enExample) * | 1976-07-13 | 1978-02-08 | ||
| US4167565A (en) * | 1976-11-08 | 1979-09-11 | Abbott Laboratories | Adenosine-5'-carboxamides and method of use |
| US5310731A (en) * | 1984-06-28 | 1994-05-10 | Whitby Research, Inc. | N-6 substituted-5'-(N-substitutedcarboxamido)adenosines as cardiac vasodilators and antihypertensive agents |
| LU87181A1 (fr) * | 1987-04-06 | 1988-11-17 | Sandoz Sa | Nouveaux derives de l'acide furannuronique,leur preparation et leur utilisation comme medicaments |
-
1987
- 1987-12-04 NL NL8702926A patent/NL8702926A/nl not_active Application Discontinuation
- 1987-12-04 HU HU875452A patent/HU198950B/hu not_active IP Right Cessation
- 1987-12-07 CH CH4763/87A patent/CH676851A5/de not_active IP Right Cessation
- 1987-12-11 BE BE8701420A patent/BE1001621A3/fr not_active IP Right Cessation
- 1987-12-12 MY MYPI87003187A patent/MY102270A/en unknown
- 1987-12-14 GR GR871895A patent/GR871895B/el unknown
- 1987-12-14 GB GB8729116A patent/GB2199036B/en not_active Expired - Lifetime
- 1987-12-14 AU AU82523/87A patent/AU601247B2/en not_active Ceased
- 1987-12-14 PH PH36210A patent/PH25421A/en unknown
- 1987-12-14 IL IL84808A patent/IL84808A/xx not_active IP Right Cessation
- 1987-12-14 DK DK655487A patent/DK655487A/da not_active Application Discontinuation
- 1987-12-14 AT AT3285/87A patent/AT393506B/de not_active IP Right Cessation
- 1987-12-14 LU LU87071A patent/LU87071A1/fr unknown
- 1987-12-14 CA CA000554261A patent/CA1291752C/en not_active Expired - Lifetime
- 1987-12-14 FR FR878717542A patent/FR2608159B1/fr not_active Expired - Lifetime
- 1987-12-14 NZ NZ222897A patent/NZ222897A/xx unknown
- 1987-12-14 US US07/132,492 patent/US4855288A/en not_active Expired - Fee Related
- 1987-12-14 SE SE8704979A patent/SE8704979L/xx not_active Application Discontinuation
- 1987-12-14 KR KR870014412A patent/KR880007533A/ko not_active Ceased
- 1987-12-14 FI FI875491A patent/FI86431C/fi not_active IP Right Cessation
- 1987-12-15 ES ES8703585A patent/ES2010736A6/es not_active Expired
- 1987-12-15 IT IT8748709A patent/IT1230116B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| SE8704979D0 (sv) | 1987-12-14 |
| US4855288A (en) | 1989-08-08 |
| IL84808A (en) | 1991-07-18 |
| CH676851A5 (enExample) | 1991-03-15 |
| AT393506B (de) | 1991-11-11 |
| ATA328587A (de) | 1991-04-15 |
| GB8729116D0 (en) | 1988-01-27 |
| HUT47594A (en) | 1989-03-28 |
| SE8704979L (sv) | 1988-06-16 |
| CA1291752C (en) | 1991-11-05 |
| DK655487D0 (da) | 1987-12-14 |
| GB2199036A (en) | 1988-06-29 |
| LU87071A1 (fr) | 1988-07-14 |
| GR871895B (en) | 1988-04-04 |
| BE1001621A3 (fr) | 1989-12-19 |
| FR2608159B1 (fr) | 1990-06-08 |
| PH25421A (en) | 1991-07-01 |
| AU601247B2 (en) | 1990-09-06 |
| FI875491L (fi) | 1988-06-16 |
| FI86431B (fi) | 1992-05-15 |
| ES2010736A6 (es) | 1989-12-01 |
| FI875491A0 (fi) | 1987-12-14 |
| KR880007533A (ko) | 1988-08-27 |
| HU198950B (en) | 1989-12-28 |
| AU8252387A (en) | 1988-06-16 |
| IT1230116B (it) | 1991-10-07 |
| NL8702926A (nl) | 1988-07-01 |
| MY102270A (en) | 1992-05-15 |
| NZ222897A (en) | 1990-02-26 |
| FR2608159A1 (fr) | 1988-06-17 |
| DK655487A (da) | 1988-06-16 |
| IL84808A0 (en) | 1988-06-30 |
| IT8748709A0 (it) | 1987-12-15 |
| GB2199036B (en) | 1990-07-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: SANDOZ AG |