JPS5970653A - 眼圧低下剤 - Google Patents

眼圧低下剤

Info

Publication number: JPS5970653A
Authority: JP; Japan
Prior art keywords: compound; group; formula; intraocular pressure; reducing agent
Prior art date: 1982-10-15
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.): Granted

Application number

JP57181948A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6330283B2 (2

Inventor

Yoshikazu Oka

岡　良和

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SENJIYU SEIYAKU KK

Senju Pharmaceutical Co Ltd

Takeda Pharmaceutical Co Ltd

Original Assignee

SENJIYU SEIYAKU KK

Senju Pharmaceutical Co Ltd

Takeda Chemical Industries 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.)

1982-10-15

Filing date

1982-10-15

Publication date

1984-04-21

1982-10-15 Application filed by SENJIYU SEIYAKU KK, Senju Pharmaceutical Co Ltd, Takeda Chemical Industries Ltd filed Critical SENJIYU SEIYAKU KK

1982-10-15 Priority to JP57181948A priority Critical patent/JPS5970653A/ja

1983-10-05 Priority to US06/538,805 priority patent/US4559361A/en

1983-10-12 Priority to GB08327342A priority patent/GB2128192B/en

1983-10-13 Priority to DE19833337185 priority patent/DE3337185A1/de

1983-10-14 Priority to FR8316420A priority patent/FR2534577B1/fr

1984-04-21 Publication of JPS5970653A publication Critical patent/JPS5970653A/ja

1988-06-17 Publication of JPS6330283B2 publication Critical patent/JPS6330283B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title abstract description 23
230000004410 intraocular pressure Effects 0.000 title abstract description 9
239000003638 chemical reducing agent Substances 0.000 title abstract 3
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 6
-1 naphthalene carboxamide compound Chemical class 0.000 claims description 14
239000000243 solution Substances 0.000 abstract description 12
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 6
238000000034 method Methods 0.000 abstract description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 4
125000000217 alkyl group Chemical group 0.000 abstract description 4
239000003889 eye drop Substances 0.000 abstract description 4
229910052697 platinum Inorganic materials 0.000 abstract description 3
239000006196 drop Substances 0.000 abstract description 2
231100000053 low toxicity Toxicity 0.000 abstract description 2
239000003960 organic solvent Substances 0.000 abstract description 2
229910052763 palladium Inorganic materials 0.000 abstract description 2
125000003118 aryl group Chemical group 0.000 abstract 2
XXYWDBWJYVWGCQ-QROXDHQXSA-N (5r,6r)-2,5-dihydroxy-6-(4-phenylbutan-2-ylamino)-5,6,7,8-tetrahydronaphthalene-1-carboxamide;hydrochloride Chemical compound Cl.N([C@H]1[C@@H](C2=C(C(=C(O)C=C2)C(N)=O)CC1)O)C(C)CCC1=CC=CC=C1 XXYWDBWJYVWGCQ-QROXDHQXSA-N 0.000 abstract 1
208000010412 Glaucoma Diseases 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
239000013078 crystal Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
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 5
239000002253 acid Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 2
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
YPFNIPKMNMDDDB-UHFFFAOYSA-K 2-[2-[bis(carboxylatomethyl)amino]ethyl-(2-hydroxyethyl)amino]acetate;iron(3+) Chemical compound [Fe+3].OCCN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O YPFNIPKMNMDDDB-UHFFFAOYSA-K 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
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
OKAOHZZUPGSGSG-UHFFFAOYSA-N 5-hydroxyimino-2-phenylmethoxy-7,8-dihydro-6h-naphthalene-1-carboxamide Chemical compound C1=CC=2C(=NO)CCCC=2C(C(=O)N)=C1OCC1=CC=CC=C1 OKAOHZZUPGSGSG-UHFFFAOYSA-N 0.000 description 1
GIHYKVLJURZKGA-UHFFFAOYSA-N 5-oxo-2-phenylmethoxy-7,8-dihydro-6h-naphthalene-1-carboxylic acid Chemical compound C1=CC=2C(=O)CCCC=2C(C(=O)O)=C1OCC1=CC=CC=C1 GIHYKVLJURZKGA-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001676573 Minium Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
241000277331 Salmonidae Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
150000002483 hydrogen compounds Chemical class 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
229910001641 magnesium iodide Inorganic materials 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical group 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 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
229960001404 quinidine Drugs 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
150000003872 salicylic acid derivatives Chemical class 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/48—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system of the same carbon skeleton
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Organic Chemistry (AREA)
Epidemiology (AREA)
Ophthalmology & Optometry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP57181948A 1982-10-15 1982-10-15 眼圧低下剤 Granted JPS5970653A (ja)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
JP57181948A JPS5970653A (ja)	1982-10-15	1982-10-15	眼圧低下剤
US06/538,805 US4559361A (en)	1982-10-15	1983-10-05	Naphthalenecarboxamides, their production and use
GB08327342A GB2128192B (en)	1982-10-15	1983-10-12	Naphthalenecarboxamides their production and use
DE19833337185 DE3337185A1 (de)	1982-10-15	1983-10-13	Naphthalincarboxamide, ihre herstellung und ihre verwendung
FR8316420A FR2534577B1 (fr)	1982-10-15	1983-10-14	Naphtalenecarboxamides, leur procede de preparation et leur utilisation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57181948A JPS5970653A (ja)	1982-10-15	1982-10-15	眼圧低下剤

Publications (2)

Publication Number	Publication Date
JPS5970653A true JPS5970653A (ja)	1984-04-21
JPS6330283B2 JPS6330283B2 (2)	1988-06-17

Family

ID=16109674

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57181948A Granted JPS5970653A (ja)	1982-10-15	1982-10-15	眼圧低下剤

Country Status (5)

Country	Link
US (1)	US4559361A (2)
JP (1)	JPS5970653A (2)
DE (1)	DE3337185A1 (2)
FR (1)	FR2534577B1 (2)
GB (1)	GB2128192B (2)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS62178514A (ja) *	1986-01-31	1987-08-05	Senjiyu Seiyaku Kk	眼局所投与用眼圧降下剤

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3623941A1 (de) *	1986-07-16	1988-01-28	Bayer Ag	Substituierte amino-5,6,7,8-tetrahydronaphthyl-oxyessigsaeuren, verfahren zu deren herstellung sowie die verwendung als arzneimittel
EP0471515B1 (en) *	1990-08-15	1997-03-05	Eli Lilly And Company	Ring-substituted 2-amino-1,2,3,4-tetra-hydronaphthalenes, 3-aminochromanes and 3-aminothiochromanes
US6197819B1 (en) *	1990-11-27	2001-03-06	Northwestern University	Gamma amino butyric acid analogs and optical isomers
US5314916A (en) *	1993-04-19	1994-05-24	Alcon Laboratories, Inc.	B2 adrenegic agonists and use thereof in the treatment of glaucoma
US5629345A (en) *	1993-07-23	1997-05-13	Vide Pharmaceuticals	Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure
US5965620A (en) *	1993-07-23	1999-10-12	Vide Pharmaceuticals	Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2029509A (en) *	1932-12-23	1936-02-04	Ici Ltd	Arylamides of 2,3-hydroxynaphthoic acids
DK254975A (da) *	1974-06-12	1975-12-13	Takeda Chemical Industries Ltd	Fremgangsmade til fremstilling af aminotetralolforbindelser
AU8194275A (en) *	1974-06-17	1976-12-16	Takeda Chemical Industries Ltd	Aminotetralin compounds
EP0026848B1 (de) *	1979-09-14	1983-05-04	Sandoz Ag	Tetralinderivate, ihre Herstellung und Heilmittel, welche diese Verbindungen enthalten
FR2512814A1 (fr) *	1981-09-16	1983-03-18	Synthelabo	Derives d'amino-2 tetrahydro-1,2,3,4 naphtalene, leur preparation et leur application en therapeutique
US4473586A (en) *	1982-05-03	1984-09-25	Abbott Laboratories	Aminoalkyl dihydronaphthalenes
US4448990A (en) *	1982-11-16	1984-05-15	Eli Lilly And Company	Hydroxyaminotetralincarboxamides

1982
- 1982-10-15 JP JP57181948A patent/JPS5970653A/ja active Granted
1983
- 1983-10-05 US US06/538,805 patent/US4559361A/en not_active Expired - Fee Related
- 1983-10-12 GB GB08327342A patent/GB2128192B/en not_active Expired
- 1983-10-13 DE DE19833337185 patent/DE3337185A1/de active Granted
- 1983-10-14 FR FR8316420A patent/FR2534577B1/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS62178514A (ja) *	1986-01-31	1987-08-05	Senjiyu Seiyaku Kk	眼局所投与用眼圧降下剤

Also Published As

Publication number	Publication date
US4559361A (en)	1985-12-17
DE3337185C2 (2)	1992-06-25
FR2534577B1 (fr)	1985-11-22
GB2128192A (en)	1984-04-26
JPS6330283B2 (2)	1988-06-17
GB8327342D0 (en)	1983-11-16
FR2534577A1 (fr)	1984-04-20
DE3337185A1 (de)	1984-04-19
GB2128192B (en)	1985-11-06

Publication	Publication Date	Title
RU2095352C1 (ru)	1997-11-10	Производное сконденсированного пиразина
EP0202164B1 (fr)	1989-02-08	Dérivés de (benzoyl-4 pipéridino)-2 phenyl-1 alcanols, leur préparation et leur application en thérapeutique
EP0288973B1 (en)	1993-01-13	Benzothiazolinone derivatives, their production and pharmaceutical composition
JPH01113356A (ja)	1989-05-02	抗高血圧剤としての非ペプチジルβ−アミノアシルアミノジオールカルバメート化合物
JPH05507720A (ja)	1993-11-04	ロイコトリエンｂ↓４アンタゴニスト
FI93013C (fi)	1995-02-10	Menetelmä terapeuttisesti käyttökelpoisten pyridopyridatsinonijohdannaisten valmistamiseksi
JPS6210508B2 (2)	1987-03-06
JPS6026373B2 (ja)	1985-06-24	抗腸瘍剤
AU2018439206B2 (en)	2024-06-06	Compounds useful as chaperone-mediated autophagy modulators
JP2023543069A (ja)	2023-10-12	ピリジニルフェニル化合物の結晶及びその製造方法
US4134991A (en)	1979-01-16	Derivatives of 2-(3-phenyl-2-aminopropionyloxy)-acetic acid
US3268582A (en)	1966-08-23	Phenylalkyl-carboxylic acid amides
JPS63295566A (ja)	1988-12-01	キノキサリノン誘導体
JPH05504360A (ja)	1993-07-08	オキソ―テトラヒドロピリダジニル―ピラゾロ［４，３―ｂ］―１，４―ベンズオキサジン
US3354201A (en)	1967-11-21	p-dihydroxybenzene-sulfonate of diethylamine
JPS6330283B2 (2)	1988-06-17
CS203184B2 (en)	1981-02-27	Process for preparing new pyrroloquinoxalinones and pyrrolobenzodiazepinones
EP0125046B1 (en)	1987-07-22	Process for preparing pyrimidinetrione derivatives
EP0718307A2 (fr)	1996-06-26	Dérivés de 1-oxo-2-(phénylsulfonyl-amino)pentylpipéridine, leur préparation et leur application en thérapeutique
US4552876A (en)	1985-11-12	Bisbenzoxazines and pharmaceutical use
CA2196102A1 (fr)	1996-02-15	Derives de streptogramine, leur preparation et les compositions pharmaceutiques qui les contiennent
JP2021535927A (ja)	2021-12-23	Ｇａｂａａ受容体アロステリック増強化合物及びその調製並びに応用
JPS582955B2 (ja)	1983-01-19	スピロ−キノロンヒダントイン類
US4116966A (en)	1978-09-26	1-Benzoxepino[4,3-c]pyridines
US2762804A (en)	1956-09-11	3-methyl-5-phenyl-2, 6-piperazinedione and derivatives thereof and method of preparing same

JPS5970653A - 眼圧低下剤 - Google Patents

Info

Links

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Landscapes

Priority Applications (5)

Applications Claiming Priority (1)

Publications (2)

Family

ID=16109674

Family Applications (1)

Country Status (5)

Cited By (1)

Families Citing this family (6)

Family Cites Families (7)

Cited By (1)

Also Published As

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