HU225905B1 - Solid-supported parallel synthesis of new carboxylic acid amide derivatives - Google Patents
Solid-supported parallel synthesis of new carboxylic acid amide derivatives Download PDFInfo
- Publication number
- HU225905B1 HU225905B1 HU0202213A HUP0202213A HU225905B1 HU 225905 B1 HU225905 B1 HU 225905B1 HU 0202213 A HU0202213 A HU 0202213A HU P0202213 A HUP0202213 A HU P0202213A HU 225905 B1 HU225905 B1 HU 225905B1
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- alkyl
- optionally substituted
- chr
- hydrogen
- Prior art date
Links
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract description 18
- 238000003786 synthesis reaction Methods 0.000 title claims description 7
- 230000015572 biosynthetic process Effects 0.000 title claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 [-CHO] Chemical group 0.000 claims abstract description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 230000003287 optical effect Effects 0.000 claims abstract description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 7
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims abstract description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims abstract description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 125000004849 alkoxymethyl group Chemical group 0.000 claims abstract description 3
- 125000004419 alkynylene group Chemical group 0.000 claims abstract description 3
- NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical compound S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 claims abstract description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 239000007790 solid phase Substances 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 239000003456 ion exchange resin Substances 0.000 claims description 5
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 150000002332 glycine derivatives Chemical class 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 3
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004970 halomethyl group Chemical group 0.000 claims description 3
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- DNUJVGBNIXGTHC-UHFFFAOYSA-N 3,6-dihydro-2h-oxazine Chemical group C1NOCC=C1 DNUJVGBNIXGTHC-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract description 6
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 abstract description 3
- XISPDFMAOWZEQG-UHFFFAOYSA-N 4h-1,4-oxazin-3-one Chemical group O=C1COC=CN1 XISPDFMAOWZEQG-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002905 alkanoylamido group Chemical group 0.000 abstract description 2
- 125000005422 alkyl sulfonamido group Chemical group 0.000 abstract description 2
- 125000001769 aryl amino group Chemical group 0.000 abstract description 2
- 125000005421 aryl sulfonamido group Chemical group 0.000 abstract description 2
- 125000002993 cycloalkylene group Chemical group 0.000 abstract description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 4
- KRLJVFYHPOGJQA-UHFFFAOYSA-N 2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]-2-oxo-n-(2-oxo-1,3-dihydroindol-5-yl)acetamide Chemical compound C1=CC(F)=CC=C1CC1CCN(C(=O)C(=O)NC=2C=C3CC(=O)NC3=CC=2)CC1 KRLJVFYHPOGJQA-UHFFFAOYSA-N 0.000 abstract 2
- UMURLIQHQSKULR-UHFFFAOYSA-N 1,3-oxazolidine-2-thione Chemical compound S=C1NCCO1 UMURLIQHQSKULR-UHFFFAOYSA-N 0.000 abstract 1
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 abstract 1
- 229940099433 NMDA receptor antagonist Drugs 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001088 anti-asthma Effects 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 230000003178 anti-diabetic effect Effects 0.000 abstract 1
- 230000000648 anti-parkinson Effects 0.000 abstract 1
- 239000000924 antiasthmatic agent Substances 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000003472 antidiabetic agent Substances 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 239000000939 antiparkinson agent Substances 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 230000000949 anxiolytic effect Effects 0.000 abstract 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 abstract 1
- 230000002051 biphasic effect Effects 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 230000001966 cerebroprotective effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 210000000548 hind-foot Anatomy 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 abstract 1
- 230000000324 neuroprotective effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000001777 nootropic effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 17
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000003480 eluent Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZVTWZSXLLMNMQC-UHFFFAOYSA-N 4-phenylmethoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 ZVTWZSXLLMNMQC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 description 1
- MENHXVNCWVKFRA-UHFFFAOYSA-N 1,4-oxazin-2-one Chemical group O=C1C=NC=CO1 MENHXVNCWVKFRA-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229940127523 NMDA Receptor Antagonists Drugs 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 238000012435 analytical chromatography Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000011176 pooling Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (34)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0202213A HU225905B1 (en) | 2002-07-10 | 2002-07-10 | Solid-supported parallel synthesis of new carboxylic acid amide derivatives |
| HRP20040178AA HRP20040178B1 (hr) | 2001-07-24 | 2002-07-23 | Derivati piperidina kao antagonisti nmda receptora |
| EA200400213A EA010162B1 (ru) | 2001-07-24 | 2002-07-23 | Амидные производные карбоновых кислот |
| KR1020047001042A KR100890676B1 (ko) | 2001-07-24 | 2002-07-23 | 신규한 카르복시산 아미드 화합물 |
| EEP200400058A EE05429B1 (et) | 2001-07-24 | 2002-07-23 | Karbokslhappe amiidi derivaadid, nende saamise meetod ning kasutamine |
| CA2453383A CA2453383C (en) | 2001-07-24 | 2002-07-23 | Piperidine derivatives as nmda receptor antagonists |
| MXPA04000737A MXPA04000737A (es) | 2001-07-24 | 2002-07-23 | Derivados de piperidina como antagonistas receptores de nmda. |
| IL159393A IL159393A (en) | 2001-07-24 | 2002-07-23 | Piperidine derivatives, pharmaceutical compositions containing them, processes for their preparation and uses thereof |
| JP2003515518A JP4322113B2 (ja) | 2001-07-24 | 2002-07-23 | 新規カルボン酸アミド化合物 |
| AU2002313566A AU2002313566B2 (en) | 2001-07-24 | 2002-07-23 | Piperidine derivatives as NMDA receptor antagonists |
| PCT/HU2002/000071 WO2003010159A1 (en) | 2001-07-24 | 2002-07-23 | Piperidine derivatives as nmda receptor antagonists |
| SK102-2004A SK287726B6 (en) | 2001-07-24 | 2002-07-23 | Carboxylic acid amide derivatives, their preparation, pharmaceutical compositions containing them and process for preparing pharmaceutical compositions |
| PT02753161T PT1409477E (pt) | 2001-07-24 | 2002-07-23 | Derivados piperidina como antagonistas de receptores nmda |
| AT02753161T ATE408611T1 (de) | 2001-07-24 | 2002-07-23 | Piperidine als nmda-rezeptorantagonisten |
| DK02753161T DK1409477T3 (da) | 2001-07-24 | 2002-07-23 | Piperdinderivater som NMDA receptorantagonister |
| EP02753161A EP1409477B1 (en) | 2001-07-24 | 2002-07-23 | Piperidine derivatives as nmda receptor antagonists |
| SI200230752T SI1409477T1 (sl) | 2001-07-24 | 2002-07-23 | Derivati piperidina kot antagonisti nmda-receptorjev |
| CNB028142349A CN100413860C (zh) | 2001-07-24 | 2002-07-23 | 作为nmda受体拮抗剂的哌啶衍生物 |
| CZ2004233A CZ2004233A3 (cs) | 2001-07-24 | 2002-07-23 | Nové amidové sloučeniny karboxylové kyseliny |
| ES02753161T ES2312603T3 (es) | 2001-07-24 | 2002-07-23 | Derivados de piperidina como antagonistas del receptor nmda. |
| BR0211393-7A BR0211393A (pt) | 2001-07-24 | 2002-07-23 | Derivados de piperidina como antagonistas de receptor nmda |
| HK04106165.2A HK1063464B (en) | 2001-07-24 | 2002-07-23 | Piperidine derivatives as nmda receptor antagonists |
| DE60228969T DE60228969D1 (enrdf_load_stackoverflow) | 2001-07-24 | 2002-07-23 | |
| NZ530055A NZ530055A (en) | 2001-07-24 | 2002-07-23 | Piperidine derivatives as NMDA receptor antagonists |
| PL367259A PL216636B1 (pl) | 2001-07-24 | 2002-07-23 | Pochodne amidów kwasów karboksylowych, środek farmaceutyczny, sposób wytwarzania pochodnych amidów kwasów karboksylowych, sposób wytwarzania środka farmaceutycznego i zastosowanie pochodnych amidów kwasów karboksylowych |
| YUP-1039/03A RS50767B (sr) | 2001-07-24 | 2002-07-23 | Piperidinski derivati kao antagonisti nmda receptora |
| IS7066A IS7066A (is) | 2001-07-24 | 2003-12-05 | Afleiður piperadíns sem mótlyf viðtaka NMDA |
| UA2004021342A UA77684C2 (en) | 2001-07-24 | 2004-01-20 | Carboxylic acid amide derivatives |
| ZA2004/00417A ZA200400417B (en) | 2001-07-24 | 2004-01-20 | Piperidine derivatives as nmda receptor antagonists |
| US10/761,940 US7435744B2 (en) | 2001-07-24 | 2004-01-21 | Piperidine derivatives as NMDA receptor antagonists |
| NO20040307A NO327099B1 (no) | 2001-07-24 | 2004-01-23 | Piperidinderivater som NMDA-reseptorantagonister, fremgangsmater for fremstilling av disse, og farmasoytiske preparater inneholdende disse |
| BG108592A BG66441B1 (bg) | 2001-07-24 | 2004-02-20 | Амиди на карбоксилни киселини |
| CO04015496A CO5560570A2 (es) | 2001-07-24 | 2004-02-23 | Nuevos compuestos de amida de acido carboxilico y procedimiento para la sintesis de los mismos |
| CY20081101405T CY1109401T1 (el) | 2001-07-24 | 2008-12-03 | Παραγωγα πιπεριδινης ως ανταγωνιστες του δεκτου nmda |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0202213A HU225905B1 (en) | 2002-07-10 | 2002-07-10 | Solid-supported parallel synthesis of new carboxylic acid amide derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP0202213D0 HUP0202213D0 (enrdf_load_stackoverflow) | 2002-09-28 |
| HUP0202213A2 HUP0202213A2 (hu) | 2004-05-28 |
| HU225905B1 true HU225905B1 (en) | 2007-12-28 |
Family
ID=90001552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0202213A HU225905B1 (en) | 2001-07-24 | 2002-07-10 | Solid-supported parallel synthesis of new carboxylic acid amide derivatives |
Country Status (1)
| Country | Link |
|---|---|
| HU (1) | HU225905B1 (enrdf_load_stackoverflow) |
-
2002
- 2002-07-10 HU HU0202213A patent/HU225905B1/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0202213D0 (enrdf_load_stackoverflow) | 2002-09-28 |
| HUP0202213A2 (hu) | 2004-05-28 |
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