KR830004585A - 치환 인돌린-2-은 유도체의 제범 - Google Patents
치환 인돌린-2-은 유도체의 제범 Download PDFInfo
- Publication number
- KR830004585A KR830004585A KR1019800004336A KR800004336A KR830004585A KR 830004585 A KR830004585 A KR 830004585A KR 1019800004336 A KR1019800004336 A KR 1019800004336A KR 800004336 A KR800004336 A KR 800004336A KR 830004585 A KR830004585 A KR 830004585A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- nitro
- group
- general formula
- Prior art date
Links
- 238000006467 substitution reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 1
- 229940118662 aluminum carbonate Drugs 0.000 claims 1
- 235000012501 ammonium carbonate Nutrition 0.000 claims 1
- 239000001099 ammonium carbonate Substances 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 230000020335 dealkylation Effects 0.000 claims 1
- 238000006900 dealkylation reaction Methods 0.000 claims 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000000523 sample Substances 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- IVATZRPSACCBJT-UHFFFAOYSA-N spiro[1,2-dihydroindole-3,4'-imidazolidine] Chemical class N1CNCC11C2=CC=CC=C2NC1 IVATZRPSACCBJT-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (1)
- 본문에 상술한 바와같이, 다음 일반식(3)의 인돌린-2,3-디온을 알카리금속 사아나이드 및 알모늄 카보네이트 또는 카바메이트와 반응시키고, 다음 일반식(6)의 화합물을 일반식R2, X(R2는 R1이 페닐기 이의의 기일때와 같고, X는 할로게노 또는 아릴-또는 알킬-설포닐옥시기)인 화합물과 반응시키고, 일반식(7)의 화합물을 암모늄 카보네이트 또는 카바메이트와 반응시키고, 벤젠환 A가 비치환되거나 또는 단일 치환기를 함유하거나 또는 R1이 치환벤질기 또는 하나 또는 두개의 치환기를 함유하는 벤질기인 일반식(1)의 상용하는 화합물을 니트로화하여 벤젠환 A가 니트로치환기를 함유 하거나 또는 R1이 니트로 치환기를 함유하는 벤질기인 일반식(1)의 화합물을 제조하고, 벤젠환 A가 비치환된 상용하는 일반식(1)의 화합물을 클로로화 또는 브름확하여 벤젠환 A가 클로로 또는 의화합물을 클로로화 또는 브름화하여 벤젠환가클로로 또는 브로로치환기를 함유하는 일반식(1)의 화합물을 제조하는, 벤젠확 A및/또는 R1이 (1-4C)알콜시기를 함유하는 상응하는 일반식(1)의 화합물을 탈알킬화하여 벤젠환 A 및/또는 R1이 하이드록시기인 일반식(1)의 화합물을 제조함을 특징으로 하는바, 일반식(1) 화합물의 광학적으로 활성인 형태가 필요할때는 상기 화합물의 라세미형태를 광학적으로 활성형태인 적당한 유기염기와 반응시키고 이렇게 얻어진 염의 투공이성체 혼합물을 통상적으로 분리하여 통상적인 방법으로 산과 처리함으로서 광학적 활성형태의 상술한 화합물을 유리시키고, 제약학적으로 허용되는 염이 필요할때는 일반식(1)의 화합물을 제약학적으로 허용될 수 있는 양이온을 제공하는 적당한 염기와 통상적인 공정을 사용하여 반응시키는 것으로 구성된, 일반식(1)의 1'-치환된 스피로 [이미다졸리딘-4,3'-인돌린] 2,2',5-트리온의 제조방법.식중,R1은 1-2할로게노 치환기를 임의로 함유하는 (1-12C)칼킬, 페닐, 나프틸메틸 또는신나밀 또는 할로게노, 트릴플루오로메틸, (1-4C)알킬, (1-4C)알콕시, 니트로, 시아노 및 하이드록시로 부터 선택된 1-3-개의 치환기를 임의로 함유하는 벤질이고, 환 A는 할로게노, (1-4C)칼킬, (1-4C) 칼콕시, 니트로 및 하이드록시로 부터 선택된 하나의 치환기 또는 할로게노, (1-4C)칼킬 및 니트로로 부터 선택된 2개의 치환기를 임의로 함유하며,R3는 아실 또는 트리-[(1-4C)알킬]실리 기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019840004392A KR850001228B1 (ko) | 1979-11-13 | 1984-07-24 | 치환 인돌린-2-온 유도체의 제조방법 |
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB39235/79 | 1979-11-13 | ||
GB7939235 | 1979-11-13 | ||
GB26459/80 | 1980-08-13 | ||
GB8026459 | 1980-08-13 | ||
GB29760/80 | 1980-09-15 | ||
GB8029760 | 1980-09-15 | ||
GB32875/80 | 1980-10-10 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840004392A Division KR850001228B1 (ko) | 1979-11-13 | 1984-07-24 | 치환 인돌린-2-온 유도체의 제조방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830004585A true KR830004585A (ko) | 1983-07-16 |
KR840002213B1 KR840002213B1 (ko) | 1984-12-03 |
Family
ID=27260798
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019800004336A KR840002213B1 (ko) | 1979-11-13 | 1980-11-12 | 치환 인돌린-2-온 유도체의 제조방법 |
KR1019840004392A KR850001228B1 (ko) | 1979-11-13 | 1984-07-24 | 치환 인돌린-2-온 유도체의 제조방법 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840004392A KR850001228B1 (ko) | 1979-11-13 | 1984-07-24 | 치환 인돌린-2-온 유도체의 제조방법 |
Country Status (21)
Country | Link |
---|---|
US (1) | US4490381A (ko) |
EP (1) | EP0028906B1 (ko) |
KR (2) | KR840002213B1 (ko) |
AT (1) | ATE9697T1 (ko) |
AU (1) | AU532110B2 (ko) |
CA (1) | CA1161848A (ko) |
DD (1) | DD158401A5 (ko) |
DE (1) | DE3069372D1 (ko) |
DK (1) | DK484880A (ko) |
ES (3) | ES8205803A1 (ko) |
FI (1) | FI70023C (ko) |
GR (1) | GR71855B (ko) |
IE (1) | IE50332B1 (ko) |
IL (1) | IL61426A (ko) |
NO (1) | NO154842C (ko) |
NZ (1) | NZ195446A (ko) |
PH (1) | PH16511A (ko) |
PL (1) | PL129212B1 (ko) |
PT (1) | PT72056B (ko) |
YU (1) | YU289080A (ko) |
ZW (1) | ZW27380A1 (ko) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IE52879B1 (en) * | 1981-05-12 | 1988-03-30 | Ici Plc | Pharmaceutical spiro-hydantoin derivatives |
ZA832679B (en) * | 1982-05-07 | 1983-12-28 | Ici Plc | Indoline derivatives |
GB2119797B (en) * | 1982-05-11 | 1985-09-04 | Ici Plc | Fluoroalkyl derivatives |
AU566869B2 (en) * | 1982-05-11 | 1987-11-05 | Imperial Chemical Industries Plc | Spiro (imidazolidine-4,3'-indoline) 2,2',5-triones |
GB8331194D0 (en) * | 1982-12-20 | 1983-12-29 | Ici Plc | Chemical process |
GB8312379D0 (en) * | 1983-05-05 | 1983-06-08 | Ici Plc | Heterocyclic compounds |
US4533667A (en) * | 1983-05-25 | 1985-08-06 | Pfizer Inc. | Imidazolidinedione derivatives |
US4464380A (en) * | 1983-05-25 | 1984-08-07 | Pfizer Inc. | Imidazolidinedione derivatives |
US4567278A (en) * | 1984-03-26 | 1986-01-28 | Imperial Chemical Industries Plc | Process for racemizing certain spiro compounds |
US4762839A (en) * | 1985-06-06 | 1988-08-09 | Tanabe Seiyaku Co., Ltd. | Quinazolinone copmpounds useful for the prophyloxis and treatment of diabetic complications |
JPS63132889A (ja) * | 1986-11-21 | 1988-06-04 | Tanabe Seiyaku Co Ltd | キナゾリノン誘導体 |
WO1992007830A2 (en) * | 1990-10-29 | 1992-05-14 | Pfizer Inc. | Oxindole peptide antagonists |
FR2708606B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés du N-phénylalkylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
AR059265A1 (es) | 2006-02-07 | 2008-03-19 | Astrazeneca Ab | Compuestos espiro condensados con actividad inhibitoria en el receptor vaniloide1 (vr1) |
WO2007091948A2 (en) * | 2006-02-07 | 2007-08-16 | Astrazeneca Ab | Novel spiro [imidazolidine-4, 3´-indole] 2, 2´,5´(1h) triones for treatment of conditions associated with vanilloid receptor 1 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2683718A (en) * | 1952-01-11 | 1954-07-13 | Searle & Co | Spiro-[xanthene-9, 4'-imidazolidine]-2, 5-dione |
JPS50137976A (ko) * | 1974-04-23 | 1975-11-01 | ||
SE422371B (sv) * | 1975-12-12 | 1982-03-01 | Aminkemi Ab | Sett att generera en ph-funktion for anvendning vid elektrofores |
US4117230A (en) * | 1976-10-18 | 1978-09-26 | Pfizer Inc. | Hydantoin derivatives as therapeutic agents |
US4147795A (en) * | 1977-02-11 | 1979-04-03 | Pfizer Inc. | Hydantoin derivatives as therapeutic agents |
US4130714A (en) * | 1977-05-23 | 1978-12-19 | Pfizer Inc. | Hydantoin therapeutic agents |
US4127665A (en) * | 1978-01-18 | 1978-11-28 | Pfizer Inc. | Thienohydantoin derivatives |
US4147797A (en) * | 1978-08-11 | 1979-04-03 | Pfizer Inc. | Spiro-furanohydantoin derivatives |
US4181728A (en) * | 1978-11-16 | 1980-01-01 | Pfizer Inc. | Spiro-polycyclicimidazolidinedione derivatives |
US4176185A (en) * | 1979-01-22 | 1979-11-27 | Pfizer Inc. | Spiro-quinolylhydantoins |
US4181729A (en) * | 1979-03-21 | 1980-01-01 | Pfizer Inc. | Phenyl or phenoxy substituted spiro-imidazolidinedione derivatives |
US4193996A (en) * | 1979-04-04 | 1980-03-18 | Pfizer Inc. | Spiro-quinolone hydantoins |
US4248882A (en) * | 1980-02-12 | 1981-02-03 | Pfizer Inc. | Treating diabetes-associated complications with hydantoin amines |
-
1980
- 1980-10-29 IE IE2239/80A patent/IE50332B1/en not_active IP Right Cessation
- 1980-10-29 US US06/201,973 patent/US4490381A/en not_active Expired - Lifetime
- 1980-10-29 AU AU63813/80A patent/AU532110B2/en not_active Ceased
- 1980-10-31 AT AT80303890T patent/ATE9697T1/de active
- 1980-10-31 DE DE8080303890T patent/DE3069372D1/de not_active Expired
- 1980-10-31 EP EP80303890A patent/EP0028906B1/en not_active Expired
- 1980-11-03 GR GR63268A patent/GR71855B/el unknown
- 1980-11-03 NZ NZ195446A patent/NZ195446A/xx unknown
- 1980-11-04 CA CA000363966A patent/CA1161848A/en not_active Expired
- 1980-11-06 IL IL61426A patent/IL61426A/xx not_active IP Right Cessation
- 1980-11-10 ZW ZW273/80A patent/ZW27380A1/xx unknown
- 1980-11-11 PH PH24843A patent/PH16511A/en unknown
- 1980-11-12 PL PL1980227789A patent/PL129212B1/pl unknown
- 1980-11-12 KR KR1019800004336A patent/KR840002213B1/ko active IP Right Grant
- 1980-11-12 YU YU02890/80A patent/YU289080A/xx unknown
- 1980-11-12 NO NO803411A patent/NO154842C/no unknown
- 1980-11-12 DD DD80225136A patent/DD158401A5/de unknown
- 1980-11-12 FI FI803539A patent/FI70023C/fi not_active IP Right Cessation
- 1980-11-13 DK DK484880A patent/DK484880A/da not_active Application Discontinuation
- 1980-11-13 ES ES496811A patent/ES8205803A1/es not_active Expired
- 1980-11-13 PT PT72056A patent/PT72056B/pt not_active IP Right Cessation
-
1981
- 1981-12-01 ES ES507616A patent/ES507616A0/es active Granted
- 1981-12-01 ES ES507617A patent/ES507617A0/es active Granted
-
1984
- 1984-07-24 KR KR1019840004392A patent/KR850001228B1/ko active IP Right Grant
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