SE447994B - Teobrominderivat och en farmaceutisk komposition med kerlutvidgande, psykotrop eller analgetisk verkan - Google Patents

Teobrominderivat och en farmaceutisk komposition med kerlutvidgande, psykotrop eller analgetisk verkan

Info

Publication number: SE447994B
Authority: SE; Sweden
Prior art keywords: formula; group; compound according; compound; compounds
Prior art date: 1979-03-05

Application number

SE8001682A

Other languages

English (en)

Swedish (sv)

Other versions

SE8001682L (sv

Inventor

H Sugimoto

S Hamano

T Shoji

T Kaneko

T Uzuo

Original Assignee

Eisai Co Ltd

Priority date (The priority date 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 date listed.)

1979-03-05

Filing date

1980-03-04

Publication date

1987-01-12

1980-03-04 Application filed by Eisai Co Ltd filed Critical Eisai Co Ltd

1980-09-06 Publication of SE8001682L publication Critical patent/SE8001682L/xx

1987-01-12 Publication of SE447994B publication Critical patent/SE447994B/sv

Links

230000000202 analgesic effect Effects 0.000 title claims description 6
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical class CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 title description 10
150000001875 compounds Chemical class 0.000 claims description 65
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
230000000506 psychotropic effect Effects 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 2
230000000304 vasodilatating effect Effects 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 2
125000004076 pyridyl group Chemical group 0.000 claims 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 1
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 20
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
241000699670 Mus sp. Species 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
230000000694 effects Effects 0.000 description 14
230000017531 blood circulation Effects 0.000 description 13
229930008281 A03AD01 - Papaverine Natural products 0.000 description 10
229960001789 papaverine Drugs 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
239000000203 mixture Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 5
210000004369 blood Anatomy 0.000 description 5
239000008280 blood Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
229960004559 theobromine Drugs 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
229920000084 Gum arabic Polymers 0.000 description 4
241000978776 Senegalia senegal Species 0.000 description 4
239000000205 acacia gum Substances 0.000 description 4
235000010489 acacia gum Nutrition 0.000 description 4
230000006399 behavior Effects 0.000 description 4
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 4
229960001076 chlorpromazine Drugs 0.000 description 4
239000013078 crystal Substances 0.000 description 4
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 4
229960003529 diazepam Drugs 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
238000000034 method Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
206010001488 Aggression Diseases 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
229940126062 Compound A Drugs 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000016571 aggressive behavior Effects 0.000 description 3
208000012761 aggressive behavior Diseases 0.000 description 3
239000000460 chlorine 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
238000002474 experimental method Methods 0.000 description 3
210000001105 femoral artery Anatomy 0.000 description 3
-1 p-toluenesulfonyloxy group Chemical group 0.000 description 3
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
210000005259 peripheral blood Anatomy 0.000 description 3
239000011886 peripheral blood Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000523 sample Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
208000002193 Pain Diseases 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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000010171 animal model Methods 0.000 description 2
230000000496 anti-anoxic effect Effects 0.000 description 2
210000001367 artery Anatomy 0.000 description 2
230000002716 ataractic effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000001771 impaired effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
229960001412 pentobarbital Drugs 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
210000002385 vertebral artery Anatomy 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
WICKLEOONJPMEQ-UHFFFAOYSA-N 1-(2-methylphenyl)piperazine Chemical compound CC1=CC=CC=C1N1CCNCC1 WICKLEOONJPMEQ-UHFFFAOYSA-N 0.000 description 1
GCEJJEYAPRULFS-UHFFFAOYSA-N 1-(3-bromopropyl)-3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCBr)C(=O)C2=C1N=CN2C GCEJJEYAPRULFS-UHFFFAOYSA-N 0.000 description 1
ANLAJHPNLDWXHU-UHFFFAOYSA-N 1-(4-bromobutyl)-3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCBr)C(=O)C2=C1N=CN2C ANLAJHPNLDWXHU-UHFFFAOYSA-N 0.000 description 1
KLWQGZODUQLBCJ-UHFFFAOYSA-N 1-(5-bromopentyl)-3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCCCBr)C(=O)C2=C1N=CN2C KLWQGZODUQLBCJ-UHFFFAOYSA-N 0.000 description 1
XUFLZPFWTDGFEG-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-1,4-diazepane Chemical compound C1=CC(Cl)=CC=C1CN1CCNCCC1 XUFLZPFWTDGFEG-UHFFFAOYSA-N 0.000 description 1
ARWGGDUMLIBRND-UHFFFAOYSA-N 1-methoxy-4-phenylpiperazine Chemical compound C1CN(OC)CCN1C1=CC=CC=C1 ARWGGDUMLIBRND-UHFFFAOYSA-N 0.000 description 1
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-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
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000905957 Channa melasoma Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
JLNTWVDSQRNWFU-UHFFFAOYSA-N OOOOOOO Chemical compound OOOOOOO JLNTWVDSQRNWFU-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-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
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
229960002319 barbital Drugs 0.000 description 1
FTOAOBMCPZCFFF-UHFFFAOYSA-N barbitone sodium Natural products CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
210000004556 brain Anatomy 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
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
239000008298 dragée Substances 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
230000002708 enhancing effect Effects 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
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000005843 halogen group Chemical group 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
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 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
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
231100000053 low toxicity Toxicity 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003973 paint Substances 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
239000006187 pill Substances 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
229940001470 psychoactive drug Drugs 0.000 description 1
239000004089 psychotropic agent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012488 sample solution Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
229940116269 uric acid Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—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
- 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
- C07D491/10—Spiro-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/10—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 3 and 7, e.g. theobromine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

SE8001682A 1979-03-05 1980-03-04 Teobrominderivat och en farmaceutisk komposition med kerlutvidgande, psykotrop eller analgetisk verkan SE447994B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2457079A JPS55118488A (en)	1979-03-05	1979-03-05	Theobromine derivative and its preparation

Publications (2)

Publication Number	Publication Date
SE8001682L SE8001682L (sv)	1980-09-06
SE447994B true SE447994B (sv)	1987-01-12

Family

ID=12141814

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8001682A SE447994B (sv)	1979-03-05	1980-03-04	Teobrominderivat och en farmaceutisk komposition med kerlutvidgande, psykotrop eller analgetisk verkan

Country Status (12)

Country	Link
US (1)	US4493837A (fr)
JP (1)	JPS55118488A (fr)
BE (1)	BE882044A (fr)
CA (1)	CA1139750A (fr)
CH (1)	CH642659A5 (fr)
DE (1)	DE3008318A1 (fr)
ES (1)	ES8104289A1 (fr)
FR (1)	FR2450831A1 (fr)
GB (1)	GB2046741B (fr)
IT (1)	IT1130292B (fr)
NL (1)	NL8001304A (fr)
SE (1)	SE447994B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5618983A (en) *	1979-07-25	1981-02-23	Eisai Co Ltd	Theophylline derivative and its preapration
US4426383A (en) *	1980-09-04	1984-01-17	Eisai Co., Ltd.	Theophylline and theobromine derivatives
US4374837A (en) *	1981-07-31	1983-02-22	Laroche Navarron, S.A.	Piperazine derivatives of theobromine
JPS58148820A (ja) *	1982-02-26	1983-09-05	Eisai Co Ltd	テオブロミン誘導体を有効成分とする脳循環代謝改善剤
FR2531085A1 (fr) *	1982-07-28	1984-02-03	Adir	Nouveaux derives de la xanthine, leur procede de preparation et les compositions pharmaceutiques les renfermant
IT1215251B (it) *	1985-03-14	1990-01-31	Ellem Ind Farmaceutica	Farmaceutiche che li contengono. composti ad attivita'antiaggregante piastrinica, procedimento per la loro preparazione e composizioni
US4810706A (en) *	1985-12-20	1989-03-07	Recherche Syntex	Piperazine derivatives of theophylline and theobromine
US4716165A (en) *	1986-09-24	1987-12-29	American Home Products Corporation	Histamine H1 antagonists
US6476041B1 (en) *	1999-10-29	2002-11-05	Merck & Co., Inc.	1,4 substituted piperidinyl NMDA/NR2B antagonists
NZ731344A (en)	2014-10-09	2018-08-31	Guangdong Raynovent Biotech Co Ltd	Hydroxyl purine compounds and applications thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1620576A1 (de) *	1966-11-25	1970-02-26	Troponwerke Dinklage & Co	Verfahren zur Herstellung von Theophyllin- und Theobrominverbindungen
DE2401254A1 (de) *	1974-01-11	1975-11-27	Boehringer Mannheim Gmbh	Neue derivate von n hoch 6-substituierten adeninen

1979
- 1979-03-05 JP JP2457079A patent/JPS55118488A/ja active Pending
1980
- 1980-03-04 ES ES489184A patent/ES8104289A1/es not_active Expired
- 1980-03-04 GB GB8007211A patent/GB2046741B/en not_active Expired
- 1980-03-04 NL NL8001304A patent/NL8001304A/nl not_active Application Discontinuation
- 1980-03-04 DE DE19803008318 patent/DE3008318A1/de not_active Ceased
- 1980-03-04 BE BE2/58443A patent/BE882044A/fr not_active IP Right Cessation
- 1980-03-04 SE SE8001682A patent/SE447994B/sv not_active IP Right Cessation
- 1980-03-05 CA CA000347069A patent/CA1139750A/fr not_active Expired
- 1980-03-05 FR FR8004899A patent/FR2450831A1/fr active Granted
- 1980-03-05 CH CH173180A patent/CH642659A5/fr not_active IP Right Cessation
- 1980-03-05 IT IT20358/80A patent/IT1130292B/it active
1982
- 1982-10-20 US US06/435,518 patent/US4493837A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ES489184A0 (es)	1981-03-16
ES8104289A1 (es)	1981-03-16
DE3008318A1 (de)	1980-09-18
GB2046741A (en)	1980-11-19
CH642659A5 (fr)	1984-04-30
IT1130292B (it)	1986-06-11
IT8020358A0 (it)	1980-03-05
SE8001682L (sv)	1980-09-06
JPS55118488A (en)	1980-09-11
FR2450831A1 (fr)	1980-10-03
BE882044A (fr)	1980-09-04
FR2450831B1 (fr)	1983-07-08
NL8001304A (nl)	1980-09-09
GB2046741B (en)	1983-06-15
CA1139750A (fr)	1983-01-18
US4493837A (en)	1985-01-15

Legal Events

Date

Code

Title

Description

1995-01-31

NUG

Patent has lapsed

Ref document number: 8001682-7

Effective date: 19921005

Format of ref document f/p: F

Publication	Publication Date	Title
SU1056902A3 (ru)	1983-11-23	Способ получени производных @ -гетероциклил-4-пиперидинаминов или их солей
DE60115937T2 (de)	2006-06-29	Piperidinverbindungen zur verwendung als antiallergika
DE60319813T2 (de)	2009-04-23	1-(4-piperidinyl)benzimidazole als histamin h3 antagonisten
KR100660309B1 (ko)	2006-12-22	시아노페닐 유도체
AU2005297799B2 (en)	2009-04-09	3-carbamoyl-2-pyridone derivative
DE3781845T2 (de)	1993-02-18	Benzimidazol-derivate.
EP3781563B1 (fr)	2022-06-29	Inhibiteurs d'hpk1, procédé de préparation et utilisation associés
KR20230043943A (ko)	2023-03-31	Cdk7 키나아제 억제제로서의 화합물 및 이의 용도
JPH11513382A (ja)	1999-11-16	５員複素環化合物、これらの化合物を含む医薬品、それらの使用及びそれらの調製方法
SK31793A3 (en)	1993-09-08	Pyridine and pyridine n-oxide derivatives of diaryl methyl piperidines and piperazines and compositions and methods of use thereof
SE456910B (sv)	1988-11-14	7-substituerad teofyllin, saett att framstaella denna och en farmaceutisk komposition
DE2656344A1 (de)	1977-07-07	Ergolinderivate, ihre verwendung und herstellung
SE465220B (sv)	1991-08-12	Piperazinsubstituerade estrar och amider av dihydropyridindikarboxylsyror, saett att framstaella dessa och en farmaceutisk komposition
JPS5826877A (ja)	1983-02-17	チアゾリジニルアルキレンピペラジン誘導体
DE2652201A1 (de)	1977-06-02	Benzisothiazolone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
CH666033A5 (de)	1988-06-30	1,4-dihydropyridinderivate und deren salze und hydrate, verfahren zur herstellung dieser verbindungen und solche verbindungen enthaltende pharmazeutische praeparate.
JPH0761968A (ja)	1995-03-07	ヘテロ環を含有する尿素誘導体
CH649995A5 (de)	1985-06-28	Piperazinderivate, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten.
SE452615B (sv)	1987-12-07	Piperazinderivat och forfaranden for framstellning derav
CS255877B2 (en)	1988-03-15	Process for preparing 1,2,4-triazolocarbamates
JPS63280077A (ja)	1988-11-17	抗不整脈剤
US3565896A (en)	1971-02-23	Pyridinecarbonyl derivatives of 7-(omega-(n-alkyl-n-optionally hydroxyalkyl substituted amino) - hydroxyalkyl)theophylline
US4493837A (en)	1985-01-15	Theobromine derivatives
EP0409048A2 (fr)	1991-01-23	2-Aminothiazoles substitués par un aminoalcoyle et médicaments les contenant
CZ290326B6 (cs)	2002-07-17	N-[3-[[2-(3,4-Dimethoxyfenyl)ethyl]amino]propyl]-4-nitrobenzamid a farmaceutický prostředek obsahující tuto sloučeninu