JPH0455190B2 - - Google Patents

Info

Publication number: JPH0455190B2
Authority: JP; Japan
Prior art keywords: spiro; dione; formula; fluorene; imidazolidine
Prior art date: 1983-04-11
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 - Lifetime

Application number

JP58501791A

Other languages

English (en)

Japanese (ja)

Other versions

JPS59500618A (ja

Inventor

Birii Marei Juniaa Yooku

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.)

Alcon Vision LLC

Original Assignee

Alcon Laboratories Inc

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.)

1983-04-11

Filing date

1983-04-11

Publication date

1992-09-02

1983-04-11 Application filed by Alcon Laboratories Inc filed Critical Alcon Laboratories Inc

1983-04-11 Priority claimed from PCT/US1983/000546 external-priority patent/WO1983003543A1/en

1984-04-12 Publication of JPS59500618A publication Critical patent/JPS59500618A/ja

1992-09-02 Publication of JPH0455190B2 publication Critical patent/JPH0455190B2/ja

Status Granted legal-status Critical Current

Links

239000000203 mixture Substances 0.000 description 77
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
239000000047 product Substances 0.000 description 43
125000003003 spiro group Chemical group 0.000 description 43
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
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238000011282 treatment Methods 0.000 description 15
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238000001727 in vivo Methods 0.000 description 13
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WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
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WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 6
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230000002401 inhibitory effect Effects 0.000 description 6
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
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SXHKHHXFAQRZOI-UHFFFAOYSA-N 2-fluorofluoren-1-one Chemical compound C1=CC=C2C3=CC=C(F)C(=O)C3=CC2=C1 SXHKHHXFAQRZOI-UHFFFAOYSA-N 0.000 description 5
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238000009825 accumulation Methods 0.000 description 5
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CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
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ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 4
150000001323 aldoses Chemical class 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 description 4
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125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
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238000001556 precipitation Methods 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
235000010288 sodium nitrite Nutrition 0.000 description 4
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238000012453 sprague-dawley rat model Methods 0.000 description 4
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 4
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239000008096 xylene Substances 0.000 description 4
IAGDDPYFLFGQCX-UHFFFAOYSA-N 1-fluoro-9h-fluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2F IAGDDPYFLFGQCX-UHFFFAOYSA-N 0.000 description 3
BNDBYDSPAZGULI-UHFFFAOYSA-N 2,7-difluoro-9h-fluorene Chemical compound FC1=CC=C2C3=CC=C(F)C=C3CC2=C1 BNDBYDSPAZGULI-UHFFFAOYSA-N 0.000 description 3
UUPNFNCKGJOLQE-UHFFFAOYSA-N 2-[4-[[2-butyl-4-chloro-5-(hydroxymethyl)imidazol-1-yl]methyl]phenyl]benzoic acid Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C(O)=O)C=C1 UUPNFNCKGJOLQE-UHFFFAOYSA-N 0.000 description 3
CFRFHWQYWJMEJN-UHFFFAOYSA-N 9h-fluoren-2-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3CC2=C1 CFRFHWQYWJMEJN-UHFFFAOYSA-N 0.000 description 3
229940118148 Aldose reductase inhibitor Drugs 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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NFMJLOPNVZKQHV-UHFFFAOYSA-N 1,2-difluoro-9h-fluorene Chemical compound C1=CC=C2CC3=C(F)C(F)=CC=C3C2=C1 NFMJLOPNVZKQHV-UHFFFAOYSA-N 0.000 description 2
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BCWZAGZQUDMPMJ-UHFFFAOYSA-N 2-(2,3-dihydroquinolin-2-yl)acetic acid Chemical compound N=1C(CC=C2C=CC=CC12)CC(=O)O BCWZAGZQUDMPMJ-UHFFFAOYSA-N 0.000 description 1
FXSCJZNMWILAJO-UHFFFAOYSA-N 2-bromo-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3CC2=C1 FXSCJZNMWILAJO-UHFFFAOYSA-N 0.000 description 1
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Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

JP50179183A 1982-04-15 1983-04-11 スピロ―フルオロフルオレン化合物、その製造法およびアルド―スレダクターゼ活性を阻害する組成物 Granted JPS59500618A (ja)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US368632		1982-04-15
US368630		1982-04-15
US368631		1982-04-15
PCT/US1983/000546 WO1983003543A1 (en)	1982-04-15	1983-04-11	Method of inhibiting aldose reductase activity, compositions therefor and process for preparing spiro-fluorofluoren and spiro-difluorofluoren compounds

Publications (2)

Publication Number	Publication Date
JPS59500618A JPS59500618A (ja)	1984-04-12
JPH0455190B2 true JPH0455190B2 (pt)	1992-09-02

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ID=22175008

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Application Number	Title	Priority Date	Filing Date
JP50179183A Granted JPS59500618A (ja)	1982-04-15	1983-04-11	スピロ―フルオロフルオレン化合物、その製造法およびアルド―スレダクターゼ活性を阻害する組成物

Country Status (1)

Country	Link
JP (1)	JPS59500618A (pt)

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* Cited by examiner, † Cited by third party
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CN113651757B (zh) *	2021-09-16	2023-09-08	河北工业大学	一种含螺[芴-杂环]结构的空穴传输材料及其制备方法和应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4181728A (en) *	1978-11-16	1980-01-01	Pfizer Inc.	Spiro-polycyclicimidazolidinedione derivatives

1983
- 1983-04-11 JP JP50179183A patent/JPS59500618A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4181728A (en) *	1978-11-16	1980-01-01	Pfizer Inc.	Spiro-polycyclicimidazolidinedione derivatives

Also Published As

Publication number	Publication date
JPS59500618A (ja)	1984-04-12

Publication	Publication Date	Title
US4436745A (en)	1984-03-13	Method of inhibiting aldose reductase activity
US4438272A (en)	1984-03-20	Spiro-(fluoren-9,4'-imidazolidine)-2',5'-diones
FI62838C (fi)	1983-03-10	Foerfarande foer framstaellning av den nya farmaceutiskt anvaendbara hoegerroterande isomeren av en asymmetriskt spiro-hydantoinfoerening
DE60129841T2 (de)	2008-04-17	Indolderivate und deren verwendung als 5-ht2b- und 5-ht2c-rezeptorliganden
DE69627042T2 (de)	2003-11-20	Isocumarinderivate und deren verwendung in medikamenten
DE2759542C2 (pt)	1988-07-07
EP0034063B1 (en)	1983-06-22	Hydantoin amines and pharmaceutical compositions thereof
IE47726B1 (en)	1984-05-30	Thienohydantoin derivatives
DE1793206C2 (de)	1982-04-01	Benzodipyrane und Verfahren zu deren Herstellung, sowie diese Verbindungen enthaltende Arzneimittel
KR900000552B1 (ko)	1990-01-31	항알레르기 및 소염 제제와 그의 제조방법
IE48585B1 (en)	1985-03-06	Spiro-furanohydantoin derivatives,process for their preparation and pharmaceutical compositions containing them
EP0092385B1 (en)	1991-06-12	Hydantoin derivatives for use in inhibiting aldose reductase activity, compositions therefor and process for preparing spiro-fluoren compounds
US4540700A (en)	1985-09-10	Treatment of diabetic complications with certain spiro-imidazolidine-diones
JPH0455190B2 (pt)	1992-09-02
DE2427207A1 (de)	1975-01-09	Verfahren zur herstellung von kondensierten pyrrolmercapto-verbindungen
CH616935A5 (en)	1980-04-30	Process for the preparation of chromone derivatives
CA1209048A (en)	1986-08-05	Compositions of spiro-hydantoin compounds for inhibiting aldose reductase activity
EP0308792A2 (de)	1989-03-29	Azachromanderivate
EP0092386B1 (en)	1988-08-10	Hydantoin therapeutic agents
PT87307B (pt)	1992-08-31	Processo para a preparacao de quinoxalil-imidazolidino-2,4-dionas substituidas e de composicoes farmaceuticas que as contem
IE49659B1 (en)	1985-11-13	Spiro-quinolone hydantoins,pharmaceutical compositions containing them,and processes for their preparation
DK169519B1 (da)	1994-11-21	Analogifremgangsmåde til fremstilling af spiro-(fluoren-9,4'-imidazolidin)-2',5'-dioner eller farmaceutisk acceptable salte deraf
DD273381A5 (de)	1989-11-15	Verfahren zur herstellung einer spiro-azolonverbindung
DE2311020A1 (de)	1974-09-12	Substituierte benzoesaeuren und arzneimittel
DE3014775C2 (pt)	1989-06-15