DE2528360A1 - Neue pyrimidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen - Google Patents
Neue pyrimidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungenInfo
- Publication number
- DE2528360A1 DE2528360A1 DE19752528360 DE2528360A DE2528360A1 DE 2528360 A1 DE2528360 A1 DE 2528360A1 DE 19752528360 DE19752528360 DE 19752528360 DE 2528360 A DE2528360 A DE 2528360A DE 2528360 A1 DE2528360 A1 DE 2528360A1
- Authority
- DE
- Germany
- Prior art keywords
- morpholino
- general formula
- parts
- compounds
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 6
- -1 p-chlorophenoxy group Chemical group 0.000 claims description 5
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 201000001421 hyperglycemia Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 239000000203 mixture Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 5
- 230000002218 hypoglycaemic effect Effects 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 230000000871 hypocholesterolemic effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QKALNAZQIMFQEC-UHFFFAOYSA-N 2-morpholin-4-yl-1h-pyrimidine-4,6-dione Chemical compound N1C(=O)CC(=O)N=C1N1CCOCC1 QKALNAZQIMFQEC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-UHFFFAOYSA-N 0.000 description 2
- JOKTYJBXSUGYND-UHFFFAOYSA-N 2,4,6-trichloro-5-ethoxypyrimidine Chemical compound CCOC1=C(Cl)N=C(Cl)N=C1Cl JOKTYJBXSUGYND-UHFFFAOYSA-N 0.000 description 2
- BXDZWBOGMCNUSE-UHFFFAOYSA-N 2,4,6-trichloro-5-methoxypyrimidine Chemical compound COC1=C(Cl)N=C(Cl)N=C1Cl BXDZWBOGMCNUSE-UHFFFAOYSA-N 0.000 description 2
- DXHADVLGURXNED-UHFFFAOYSA-N 4-(4,6-dichloro-5-methoxypyrimidin-2-yl)morpholine Chemical compound N1=C(Cl)C(OC)=C(Cl)N=C1N1CCOCC1 DXHADVLGURXNED-UHFFFAOYSA-N 0.000 description 2
- OXCOCPRVQUEIOL-UHFFFAOYSA-N 4-(4,6-dichloropyrimidin-2-yl)morpholine Chemical compound ClC1=CC(Cl)=NC(N2CCOCC2)=N1 OXCOCPRVQUEIOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- WBTZDFMLKDSAFA-UHFFFAOYSA-N 2,3-diethoxy-3-oxopropanoic acid Chemical compound CCOC(C(O)=O)C(=O)OCC WBTZDFMLKDSAFA-UHFFFAOYSA-N 0.000 description 1
- GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 description 1
- JMQLSGNVKGFIQL-UHFFFAOYSA-N 2,4,6-trichloro-5-(4-chlorophenoxy)pyrimidine Chemical compound C1=CC(Cl)=CC=C1OC1=C(Cl)N=C(Cl)N=C1Cl JMQLSGNVKGFIQL-UHFFFAOYSA-N 0.000 description 1
- KMPDRUUXTSYMJD-UHFFFAOYSA-N 2,4,6-trichloro-5-ethylpyrimidine Chemical compound CCC1=C(Cl)N=C(Cl)N=C1Cl KMPDRUUXTSYMJD-UHFFFAOYSA-N 0.000 description 1
- VTSWSQGDJQFXHB-UHFFFAOYSA-N 2,4,6-trichloro-5-methylpyrimidine Chemical compound CC1=C(Cl)N=C(Cl)N=C1Cl VTSWSQGDJQFXHB-UHFFFAOYSA-N 0.000 description 1
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 1
- OFKJICNZVQCRSL-UHFFFAOYSA-N 2-(4-chlorophenoxy)-3-ethoxy-3-oxopropanoic acid Chemical compound CCOC(=O)C(C(O)=O)OC1=CC=C(Cl)C=C1 OFKJICNZVQCRSL-UHFFFAOYSA-N 0.000 description 1
- AHHOEWMSBSEQAQ-UHFFFAOYSA-N 3-ethoxy-2-methoxy-3-oxopropanoic acid Chemical compound CCOC(=O)C(OC)C(O)=O AHHOEWMSBSEQAQ-UHFFFAOYSA-N 0.000 description 1
- MQLQAAFDPKWTJT-UHFFFAOYSA-N 3-o-(4-chlorophenyl) 1-o-ethyl propanedioate Chemical compound CCOC(=O)CC(=O)OC1=CC=C(Cl)C=C1 MQLQAAFDPKWTJT-UHFFFAOYSA-N 0.000 description 1
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical class ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 1
- VEYSDMOATSZIIT-UHFFFAOYSA-N 4-(4,6-dichloro-5-ethoxypyrimidin-2-yl)morpholine Chemical compound N1=C(Cl)C(OCC)=C(Cl)N=C1N1CCOCC1 VEYSDMOATSZIIT-UHFFFAOYSA-N 0.000 description 1
- DKBPRRBUWNWPPL-UHFFFAOYSA-N 4-(4,6-dichloro-5-ethylpyrimidin-2-yl)morpholine Chemical compound N1=C(Cl)C(CC)=C(Cl)N=C1N1CCOCC1 DKBPRRBUWNWPPL-UHFFFAOYSA-N 0.000 description 1
- WOJQAYWVAAKEOU-UHFFFAOYSA-N 4-[4,6-dichloro-5-(4-chlorophenoxy)pyrimidin-2-yl]morpholine Chemical compound C1=CC(Cl)=CC=C1OC1=C(Cl)N=C(N2CCOCC2)N=C1Cl WOJQAYWVAAKEOU-UHFFFAOYSA-N 0.000 description 1
- GMUMNOPSIBDNAB-UHFFFAOYSA-N 5-butyl-2,4,6-trichloropyrimidine Chemical compound CCCCC1=C(Cl)N=C(Cl)N=C1Cl GMUMNOPSIBDNAB-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 241001579678 Panthea coenobita Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 230000002641 glycemic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7511154A FR2306697A1 (fr) | 1975-04-10 | 1975-04-10 | Nouvelles pyrimidines utilisables comme medicaments antidiabetiques et hypocholesterolemiants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2528360A1 true DE2528360A1 (de) | 1976-10-21 |
Family
ID=9153719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752528360 Withdrawn DE2528360A1 (de) | 1975-04-10 | 1975-06-25 | Neue pyrimidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3984411A (enExample) |
| JP (1) | JPS51118777A (enExample) |
| BE (1) | BE829845A (enExample) |
| CA (1) | CA1036597A (enExample) |
| CH (1) | CH603626A5 (enExample) |
| DE (1) | DE2528360A1 (enExample) |
| ES (1) | ES439017A1 (enExample) |
| FR (1) | FR2306697A1 (enExample) |
| GB (1) | GB1502182A (enExample) |
| IT (1) | IT1036400B (enExample) |
| LU (1) | LU72743A1 (enExample) |
| NL (1) | NL7507441A (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU176972B (hu) * | 1977-06-13 | 1981-06-28 | Gyogyszerkutato Intezet | Sposob poluchenija novykh proizvodnykh piridazinil-gidrazona |
| US4648896A (en) * | 1982-11-15 | 1987-03-10 | Ciba-Geigy Corporation | 2-aryl-4,6-dihalopyrimidines as antidote for protecting cultivated plants from phytotoxic damage caused by herbicides |
| FI895821A7 (fi) * | 1988-12-07 | 1990-06-08 | The Wellcome Foundation Ltd | Farmaseuttisesti aktivisia CNS-yhdisteitä |
| WO1999024422A1 (en) | 1997-11-05 | 1999-05-20 | Neurosearch A/S | Azaring-ether derivatives and their use as nicotinic ach receptor modulators |
| CN102558155A (zh) | 2003-01-14 | 2012-07-11 | 阿伦纳药品公司 | 作为代谢调节剂的芳基和杂芳基衍生物及其所涉及的疾病如糖尿病和高血糖症的预防和治疗 |
| DK1606282T3 (da) * | 2003-02-24 | 2009-03-16 | Arena Pharm Inc | Phenyl- og pyridylpipereidinye-derivater som modulatorer af glucosemetabolisme |
| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| CA2441775C (en) * | 2003-09-23 | 2004-09-28 | Westport Research Inc. | Container for holding a cryogenic fluid |
| DE602005011279D1 (de) * | 2004-06-04 | 2009-01-08 | Arena Pharm Inc | Substituierte aryl- und heteroarylderivate als modulatoren des stoffwechsels und für die prophylaxe und behandlung von damit in zusammenhang stehenden erkrankungen |
| DOP2006000010A (es) | 2005-01-10 | 2006-07-31 | Arena Pharm Inc | Procedimiento para preparar eteres aromáticos |
| MY148521A (en) * | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| RS20080112A (sr) * | 2005-09-16 | 2009-05-06 | Arena Pharmaceuticals Inc., | Modulatori metabolizma i lečenje poremećaja koji su vezi sa njima |
| TW200811147A (en) * | 2006-07-06 | 2008-03-01 | Arena Pharm Inc | Modulators of metabolism and the treatment of disorders related thereto |
| TW200811140A (en) * | 2006-07-06 | 2008-03-01 | Arena Pharm Inc | Modulators of metabolism and the treatment of disorders related thereto |
| DE602008005319D1 (de) | 2007-08-30 | 2011-04-14 | Dow Agrosciences Llc | 2-(substituierte phenyl)-6-amino-5-alkoxy-, thioalkoxy- und aminoalkyl-4-pyrimidincarboxylate und ihre verwendung als herbizide |
| JP5856980B2 (ja) | 2010-01-27 | 2016-02-10 | アリーナ ファーマシューティカルズ， インコーポレイテッド | （Ｒ）−２−（７−（４−シクロペンチル−３−（トリフルオロメチル）ベンジルオキシ）−１，２，３，４−テトラヒドロシクロペンタ［ｂ］インドール−３−イル）酢酸およびその塩の調製のためのプロセス |
| EP3323818A1 (en) | 2010-09-22 | 2018-05-23 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| EP4445956A3 (en) | 2015-01-06 | 2024-12-04 | Arena Pharmaceuticals, Inc. | Compound for use in treating conditions related to the s1p1 receptor |
| DK3307262T3 (da) | 2015-06-15 | 2021-08-09 | Nmd Pharma As | Forbindelser til anvendelse ved behandling af neuromuskulære lidelser |
| EP3310760B8 (en) | 2015-06-22 | 2022-10-19 | Arena Pharmaceuticals, Inc. | Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid for use in s1p1 receptor-associated disorders |
| EP3582772A1 (en) | 2017-02-16 | 2019-12-25 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| US11591284B2 (en) | 2017-12-14 | 2023-02-28 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US11730714B2 (en) | 2017-12-14 | 2023-08-22 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US12440477B2 (en) | 2017-12-14 | 2025-10-14 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US10385028B2 (en) | 2017-12-14 | 2019-08-20 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US11147788B2 (en) | 2017-12-14 | 2021-10-19 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| KR102859841B1 (ko) | 2018-06-06 | 2025-09-12 | 아레나 파마슈티칼스, 인크. | S1p1 수용체와 관련된 병태의 치료 방법 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3259623A (en) * | 1963-06-14 | 1966-07-05 | Olin Mathieson | Process for preparing 2-(secondary amino)-halogenopyrimidines |
| US3261833A (en) * | 1964-10-20 | 1966-07-19 | Smith Kline French Lab | 2,4-diamino-6-aminoalkoxy pyrimidines |
| GB1143167A (en) * | 1967-01-25 | 1969-02-19 | Ucb Sa | Derivatives of pyrimidine |
-
1975
- 1975-04-10 FR FR7511154A patent/FR2306697A1/fr active Granted
- 1975-05-23 GB GB22982/75A patent/GB1502182A/en not_active Expired
- 1975-06-04 BE BE157011A patent/BE829845A/xx not_active IP Right Cessation
- 1975-06-16 LU LU72743A patent/LU72743A1/xx unknown
- 1975-06-19 CH CH800275A patent/CH603626A5/xx not_active IP Right Cessation
- 1975-06-23 NL NL7507441A patent/NL7507441A/xx not_active Application Discontinuation
- 1975-06-25 DE DE19752528360 patent/DE2528360A1/de not_active Withdrawn
- 1975-06-27 CA CA230,309A patent/CA1036597A/fr not_active Expired
- 1975-06-30 JP JP50080752A patent/JPS51118777A/ja active Pending
- 1975-06-30 ES ES439017A patent/ES439017A1/es not_active Expired
- 1975-07-01 IT IT68679/75A patent/IT1036400B/it active
- 1975-07-17 US US05/596,880 patent/US3984411A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51118777A (en) | 1976-10-18 |
| CA1036597A (fr) | 1978-08-15 |
| CH603626A5 (enExample) | 1978-08-31 |
| ES439017A1 (es) | 1977-06-16 |
| FR2306697B1 (enExample) | 1979-08-10 |
| NL7507441A (nl) | 1976-10-12 |
| BE829845A (fr) | 1975-12-04 |
| GB1502182A (en) | 1978-02-22 |
| IT1036400B (it) | 1979-10-30 |
| US3984411A (en) | 1976-10-05 |
| FR2306697A1 (fr) | 1976-11-05 |
| LU72743A1 (enExample) | 1975-10-08 |
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