KR940007018A - 크산톤 유도체, 이의 제조방법 및 용도 - Google Patents
크산톤 유도체, 이의 제조방법 및 용도 Download PDFInfo
- Publication number
- KR940007018A KR940007018A KR1019930017472A KR930017472A KR940007018A KR 940007018 A KR940007018 A KR 940007018A KR 1019930017472 A KR1019930017472 A KR 1019930017472A KR 930017472 A KR930017472 A KR 930017472A KR 940007018 A KR940007018 A KR 940007018A
- Authority
- KR
- South Korea
- Prior art keywords
- xanthone
- alkyl
- compound
- branched
- formula
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title 1
- 150000007964 xanthones Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 7
- 125000004122 cyclic group Chemical group 0.000 claims abstract 3
- 208000006386 Bone Resorption Diseases 0.000 claims abstract 2
- 230000024279 bone resorption Effects 0.000 claims abstract 2
- 230000002401 inhibitory effect Effects 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 6
- 238000000034 method Methods 0.000 claims 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- POARTHFLPKAZBQ-UHFFFAOYSA-N 3,6-dihydroxyxanthen-9-one Chemical compound OC1=CC=C2C(=O)C3=CC=C(O)C=C3OC2=C1 POARTHFLPKAZBQ-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 150000004703 alkoxides Chemical class 0.000 claims 2
- 239000003444 phase transfer catalyst Substances 0.000 claims 2
- LICJXFCBDRPUOF-UHFFFAOYSA-N 3,6-dibutoxyxanthen-9-one Chemical compound CCCCOC1=CC=C2C(=O)C3=CC=C(OCCCC)C=C3OC2=C1 LICJXFCBDRPUOF-UHFFFAOYSA-N 0.000 claims 1
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 claims 1
- GWJKLILMJUPPGX-UHFFFAOYSA-N 3-cyclopentyloxy-6-methylxanthen-9-one Chemical compound C=1C(C)=CC=C(C(C2=CC=3)=O)C=1OC2=CC=3OC1CCCC1 GWJKLILMJUPPGX-UHFFFAOYSA-N 0.000 claims 1
- KLWFPRSIQDQPPJ-UHFFFAOYSA-N 3-methyl-6-propan-2-yloxyxanthen-9-one Chemical compound CC1=CC=C2C(=O)C3=CC=C(OC(C)C)C=C3OC2=C1 KLWFPRSIQDQPPJ-UHFFFAOYSA-N 0.000 claims 1
- KVUORIWSHOZLGF-UHFFFAOYSA-N C(CC)OC1=CC=CC=2OC3=CC(=CC=C3C(C12)=O)OCCC Chemical compound C(CC)OC1=CC=CC=2OC3=CC(=CC=C3C(C12)=O)OCCC KVUORIWSHOZLGF-UHFFFAOYSA-N 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 230000003262 anti-osteoporosis Effects 0.000 claims 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000003799 water insoluble solvent Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Physical Education & Sports Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
다음 일반식(Ⅰ)의 3,6-이치환 크산틴-9-온 유도체는 흥미있는 골흡수 저해 활성을 갖는다.
상기식에서 R=C3-C8의 알킬(직쇄, 측쇄 또는 환)이고, R1=C-C8의 알킬(직쇄, 측쇄 또는 환)또는 OR기로서, R은 상기에서 정의한 바와 같다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 골흡수 저해 활성을 갖는 다음 일반식 Ⅰ)의 3,6-이치환 크산틴-9-온 유도체.상기식에서, R=C3-C8의 알킬(직쇄, 측쇄 또는 환)이고, R1=C-C8의 알킬(직쇄, 측쇄 또는 환) 또는 R은 상기에서 정의한 바와 같은 OR기이다.
- 제2항에 있어서, 3, 6-디(이소프로폭시)크산톤, 3, 6-디(n-부톡시)-크산톤, 3, 6-디(사이클로펜틸옥시)크산톤, 3-이소프로폭시-6-n-프로폭시-크산톤,3-메틸-6-이소프로폭시-크산톤 및 3-메틸-6-사이클로펜틸옥시-크산톤으로부터 선택된 화합물.
- 3, 6-디하이드록시-크산톤(Ⅱ)이 다음식에 따라 염기의 존재하에, 과량의 동일한 알킬화제 R-X로 알킬화되거나 연속상 내에서 두가지 다른 알킬화에 R-X 및 R′-X로 알킬화되는 것을 특징으로 하는, R1-OR인 청구항 1항에 따른 일반식 Ⅰ화합물의 제조방법.상기식에서 R 및 R`는 C3-C8의 알킬(직쇄, 측쇄 또는 환)이며, X는 할로겐 원소 또는 ROSO3또는 R′OSO3 -잔기이다.
- 제3항에 있어서, 상기 반응이 극성 용매 내에서 수행되는 것을 특징으로 하는 방법.
- 제4항에 있어서, 상기 용매가 N,N′-디메틸포름아미드, 디메틸설폭시드, 아세톤 및 메틸에틸케톤으로부터 선택되는 것을 특징으로 하는 방법.
- 제5항에 있어서, 상기 반응이 상전이 촉매의 존재하, 물 및 비수용성 용매로 이루어진 이상계(biphasin system)내에서 수행되는 것을 특징으로 하는 방법.
- 일반식 Ⅳ의 3-할로겐-6-알킬-크산톤이 알콕사이드 RO-와 반응하도록 되며, 일반식 Ⅰ의 화합물은 다음식에 따라 제조되는 것을 특징으로 하는, R1=C1-C8의 알킬(직쇄, 측쇄 또는 환)인 일반식 Ⅰ 화합물의 제조방법.상기식에서 Hal=F, CI, Br, I이고 R1은 C1-C8의 알킬(직쇄, 측쇄 또는 환)이며 R은 상기에서 정의한 바와 같다.
- 제7항에 있어서, 상기 알콕사이드 RO-와 3-할로겐-6-알킬-크산톤Ⅳ사이의 반응이 70 내지 150°C온도번위에서, 임의적으로 상전이 촉매의 존재하에서 수행되는 것을 특징으로 하는 방법.
- 활성성분으로서 제1항 또는 제2항의 화합물을 포함하는 약제학적 조성물.
- 항골다공증 활성을 갖는 약제의 제조를 위한 제1항 또는 제2항의 화합물의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITM192A002071 | 1992-09-07 | ||
| ITMI92A002071 | 1992-09-07 | ||
| ITMI922071A IT1261662B (it) | 1992-09-07 | 1992-09-07 | Derivati xantonici, loro preparazione ed attivita' |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR940007018A true KR940007018A (ko) | 1994-04-26 |
| KR100279179B1 KR100279179B1 (ko) | 2001-02-01 |
Family
ID=11363916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930017472A KR100279179B1 (ko) | 1992-09-07 | 1993-09-02 | 크산톤 유도체, 이의 제조방법 및 용도 |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0586960B1 (ko) |
| JP (1) | JP3264750B2 (ko) |
| KR (1) | KR100279179B1 (ko) |
| AT (1) | ATE133948T1 (ko) |
| DE (1) | DE69301514T2 (ko) |
| DK (1) | DK0586960T3 (ko) |
| ES (1) | ES2084426T3 (ko) |
| GR (1) | GR3019373T3 (ko) |
| HK (1) | HK1007141A1 (ko) |
| IT (1) | IT1261662B (ko) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101665940B1 (ko) | 2016-07-08 | 2016-10-24 | 주식회사 세계로 | 자석을 이용한 연결부재 및 이를 포함하는 파티션 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3555043A (en) * | 1969-02-17 | 1971-01-12 | Sterling Drug Inc | Tertiary-amino-lower-alkoxy-9-benzylxanthenes and thioxanthenes |
| IE55228B1 (en) * | 1982-04-27 | 1990-07-04 | Wellcome Found | Tricyclic compounds,preparation,and use |
| US4661607A (en) * | 1984-09-21 | 1987-04-28 | Chugai Seiyaku Kabushiki Kaisha | Furoxanthone derivatives useful as diuretics |
-
1992
- 1992-09-07 IT ITMI922071A patent/IT1261662B/it active IP Right Grant
-
1993
- 1993-08-24 EP EP93113466A patent/EP0586960B1/en not_active Expired - Lifetime
- 1993-08-24 ES ES93113466T patent/ES2084426T3/es not_active Expired - Lifetime
- 1993-08-24 AT AT93113466T patent/ATE133948T1/de not_active IP Right Cessation
- 1993-08-24 DE DE69301514T patent/DE69301514T2/de not_active Expired - Fee Related
- 1993-08-24 DK DK93113466.2T patent/DK0586960T3/da active
- 1993-09-02 KR KR1019930017472A patent/KR100279179B1/ko not_active IP Right Cessation
- 1993-09-02 JP JP24199193A patent/JP3264750B2/ja not_active Expired - Fee Related
-
1996
- 1996-03-20 GR GR960400773T patent/GR3019373T3/el unknown
-
1998
- 1998-06-24 HK HK98106304A patent/HK1007141A1/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101665940B1 (ko) | 2016-07-08 | 2016-10-24 | 주식회사 세계로 | 자석을 이용한 연결부재 및 이를 포함하는 파티션 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3264750B2 (ja) | 2002-03-11 |
| DK0586960T3 (da) | 1996-07-01 |
| EP0586960B1 (en) | 1996-02-07 |
| KR100279179B1 (ko) | 2001-02-01 |
| JPH072828A (ja) | 1995-01-06 |
| ITMI922071A0 (it) | 1992-09-07 |
| ATE133948T1 (de) | 1996-02-15 |
| DE69301514D1 (de) | 1996-03-21 |
| IT1261662B (it) | 1996-05-28 |
| GR3019373T3 (en) | 1996-06-30 |
| ITMI922071A1 (it) | 1994-03-08 |
| EP0586960A1 (en) | 1994-03-16 |
| HK1007141A1 (en) | 1999-04-01 |
| ES2084426T3 (es) | 1996-05-01 |
| DE69301514T2 (de) | 1996-08-01 |
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| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 20060929 Year of fee payment: 7 |
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| LAPS | Lapse due to unpaid annual fee |