JPS6232751B2 - - Google Patents
Info
- Publication number
- JPS6232751B2 JPS6232751B2 JP11071080A JP11071080A JPS6232751B2 JP S6232751 B2 JPS6232751 B2 JP S6232751B2 JP 11071080 A JP11071080 A JP 11071080A JP 11071080 A JP11071080 A JP 11071080A JP S6232751 B2 JPS6232751 B2 JP S6232751B2
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- methyl
- pyrimidine
- pyrrolo
- dihydro
- 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.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 238000010992 reflux Methods 0.000 description 25
- 239000002904 solvent Substances 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- -1 hydrochloric acid -Acetyl-γ-butyrolactone Chemical compound 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- WQWSMVWRGAFPJX-UHFFFAOYSA-N (3-amino-1h-1,2,4-triazol-5-yl)methanol Chemical compound NC1=NNC(CO)=N1 WQWSMVWRGAFPJX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical group 0.000 description 4
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
- 230000000304 vasodilatating effect Effects 0.000 description 4
- ZMIPXFONIOFODT-UHFFFAOYSA-N 11-(chloromethyl)-7-methyl-3-(3-methylbutyl)-1,3,8,10,12-pentazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene Chemical compound N12N=C(CCl)N=C2N=C(C)C2=C1N(CCC(C)C)CC2 ZMIPXFONIOFODT-UHFFFAOYSA-N 0.000 description 3
- 206010003210 Arteriosclerosis Diseases 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
- LWCCOZINQQEWHC-UHFFFAOYSA-N N1=C2N=CNN2C2=NC=CC2=C1 Chemical class N1=C2N=CNN2C2=NC=CC2=C1 LWCCOZINQQEWHC-UHFFFAOYSA-N 0.000 description 3
- DNYDATFAPJPMQW-UHFFFAOYSA-N OC1=C(C(=NC=2N1N=C(N2)CO)C)CCO Chemical compound OC1=C(C(=NC=2N1N=C(N2)CO)C)CCO DNYDATFAPJPMQW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 3
- BSLGCRRFZJAUOD-UHFFFAOYSA-N 11-(chloromethyl)-7-methyl-3-propan-2-yl-1,3,8,10,12-pentazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene Chemical compound N12N=C(CCl)N=C2N=C(C)C2=C1N(C(C)C)CC2 BSLGCRRFZJAUOD-UHFFFAOYSA-N 0.000 description 2
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 2
- HBXOYCMKIPMRFF-UHFFFAOYSA-N 7-chloro-6-(2-chloroethyl)-2-(chloromethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound ClC1=C(CCCl)C(C)=NC2=NC(CCl)=NN21 HBXOYCMKIPMRFF-UHFFFAOYSA-N 0.000 description 2
- 206010003178 Arterial thrombosis Diseases 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 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 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- HXKYNBCJKDAHOJ-UHFFFAOYSA-N n-(3-methylbutyl)aniline Chemical compound CC(C)CCNC1=CC=CC=C1 HXKYNBCJKDAHOJ-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 description 1
- DLBVESNPXKWGKE-UHFFFAOYSA-N 1,3,8,10,12-pentazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraen-11-ylmethanamine Chemical compound NCC1=NN2C(N=CC3=C2NCC3)=N1 DLBVESNPXKWGKE-UHFFFAOYSA-N 0.000 description 1
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- HSWAMZDYEBXRAH-UHFFFAOYSA-N 3-butyl-11-(chloromethyl)-7-methyl-1,3,8,10,12-pentazatricyclo[7.3.0.02,6]dodeca-2(6),7,9,11-tetraene Chemical compound N12N=C(CCl)N=C2N=C(C)C2=C1N(CCCC)CC2 HSWAMZDYEBXRAH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 208000002720 Malnutrition Diseases 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
- FBWJLPIKVCHCTD-UHFFFAOYSA-N OCCC=1N=C2N=C(C=CN2N1)C Chemical compound OCCC=1N=C2N=C(C=CN2N1)C FBWJLPIKVCHCTD-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229960002474 hydralazine Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 238000011369 optimal treatment Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11071080A JPS5735593A (en) | 1980-08-12 | 1980-08-12 | Novel pyrolo 3,2-e -s-triazolo 1,5-a pyrimidine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11071080A JPS5735593A (en) | 1980-08-12 | 1980-08-12 | Novel pyrolo 3,2-e -s-triazolo 1,5-a pyrimidine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5735593A JPS5735593A (en) | 1982-02-26 |
| JPS6232751B2 true JPS6232751B2 (enrdf_load_stackoverflow) | 1987-07-16 |
Family
ID=14542491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11071080A Granted JPS5735593A (en) | 1980-08-12 | 1980-08-12 | Novel pyrolo 3,2-e -s-triazolo 1,5-a pyrimidine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5735593A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0101517B1 (en) * | 1982-02-19 | 1986-10-29 | Mochida Pharmaceutical Co., Ltd. | Novel s-triazole(1,5-a)pyrimidine derivatives |
| ATE493988T1 (de) | 2001-07-13 | 2011-01-15 | Btg Internat Ltd Company No 2664412 | Pyrimidinderivate enthaltendes medikament |
-
1980
- 1980-08-12 JP JP11071080A patent/JPS5735593A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5735593A (en) | 1982-02-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2525126B2 (ja) | キナゾリノン抗狭心症剤 | |
| US5698560A (en) | Imidazoquinazoline derivatives | |
| EP0674641B1 (en) | Pyrrolopyrimidines as crf antagonists | |
| RU2114113C1 (ru) | Пиразолопиримидиноны, фармацевтическая композиция и способ ингибирования фосфодиэстеразы циклического гуанозин-3',5'-монофосфата | |
| JP2531102B2 (ja) | チエノトリアゾロジアゼピン化合物からなる医薬 | |
| JP2810236B2 (ja) | ナフタレン誘導体 | |
| US5389633A (en) | Triazolopyridazine compounds, their production and use | |
| US6964960B2 (en) | Indoloquinazolinones | |
| JPS61155358A (ja) | ジアリール酪酸誘導体 | |
| JP2753659B2 (ja) | ピラゾール誘導体 | |
| JPH0283375A (ja) | ２−置換ピペラジニル−２−（１，２−ベンズイソキサゾール−３−イル）酢酸誘導体 | |
| US6077841A (en) | 5-heterocyclyl pyrazolo[4,3-d]pyrimidin-7-ones for the treatment of male erectile dysfunction | |
| JP3937367B2 (ja) | 一酸化窒素合成酵素阻害剤 | |
| JPH02138266A (ja) | ６‐フェニル‐３‐（ピペラジニルアルキル）‐２，４（１ｈ，３ｈ）‐ピリミジンジオン誘導体 | |
| EP0089065B1 (en) | Novel phenylpiperazine derivatives and process for producing the same | |
| EP0023350A1 (en) | Theophylline derivatives, a process for the preparation of the same and a therapeutical composition | |
| KR930005175B1 (ko) | 4,7-디히드로티에노 [2,3-b] 피리딘 유도체의 제조방법 | |
| EP0562440B1 (en) | Imidazopyridazines as antiasthmatics | |
| JPS5865292A (ja) | 新規なトリアゾロキナゾロン誘導体及びそれらの塩類、これらの製造法並びにこれらを含む組成物 | |
| JPS6232751B2 (enrdf_load_stackoverflow) | ||
| EP0101517B1 (en) | Novel s-triazole(1,5-a)pyrimidine derivatives | |
| DE69121894T2 (de) | Heterocyclische verbindungen, herstellung und verwendung | |
| US4112092A (en) | 1-Naphthylmethyl-4-(thiazolyl-2)-piperazines | |
| JPS6346756B2 (enrdf_load_stackoverflow) | ||
| JPH07330767A (ja) | シクロヘキサン誘導体、その製造法および疾患の治療におけるその使用 |