KR100697361B1 - 세포 내 침투를 촉진하는 지방족 모노아민 또는 양이온성중합체를 포함하는 수화층판상 또는 리포좀, 그것의스크리닝 방법 및 이를 포함하는 화장료 혹은 약제학적조성물 - Google Patents
세포 내 침투를 촉진하는 지방족 모노아민 또는 양이온성중합체를 포함하는 수화층판상 또는 리포좀, 그것의스크리닝 방법 및 이를 포함하는 화장료 혹은 약제학적조성물 Download PDFInfo
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- KR100697361B1 KR100697361B1 KR1020040104333A KR20040104333A KR100697361B1 KR 100697361 B1 KR100697361 B1 KR 100697361B1 KR 1020040104333 A KR1020040104333 A KR 1020040104333A KR 20040104333 A KR20040104333 A KR 20040104333A KR 100697361 B1 KR100697361 B1 KR 100697361B1
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- Prior art keywords
- liposome
- quaternized
- substance
- liposomes
- intracellular penetration
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Abstract
Description
다른 구체예에 따르면, 세포 내 침투 시 실질적으로 활성이 없는 형광 화합물은 상기 배양섬유아세포에 자발적으로는 침투하지 않는 형광 화합물이다.
프로브 명칭 | 특징 | Exc/Em | 농도 | 캡슐화여부 | 누수 | 세포투과 | 독성 | 리포좀 내 침투 | 보유(retained) |
#L7545L Lysosensor yellow/blue DND 160 | pH에 민감함 | 329/440 | 10μM | Y | Y | Y | N | N | N |
#H-348 hydroxypyrene trisulfonic acid, trisodium salt | 403/511 | 1mM | N | NT | N | NT | N | N | |
#P-12925 pentafluorobenzoylamino fluorescein | 492/516 | 200μM | Y | N | N | Y | Y | ||
#F-1200 Fura-2.pentapotassium salt | Ca2+민감 | 335/505 | 10μM | N | N | N | N | Y | |
#C-369 carboxy dichlorofluorescein | 에스터라아제가 있는 경우 형광을 띰 | 85μM | Y | Y | Y | NT | NT | N | |
#B-1151 carboxyethyl carboxyfluorescein | 482/520 | 50μM | N | NT | ? | NT | NT | N | |
#T-490 tetramethylrhodamine isothiocyanate TRITC | 555/580 | Y | ? | ? | N | Y | PEI의 방해 없음 | ||
#C-687 cascade blue hydrazine trisodium salt | 399/421 | 200μM | Y | NT | N | N | Very low | N | |
#S-1129 sulfo fluorescein diacetate | 200μM | NT | NT | N | N | Very low | N | ||
#D-3329 dextran texas red | 592/609 | NT | NT | N | Y | N | N |
세포독성 (무처리 대조군에 대한 %) | 침투(프로브 없음) | 침투(세척 후 형광) | |
PFB-F(485-530) | 110.7% | 8(45 증가) | 65(45 증가) |
TRITC(530-620) | 74.8 | 295(50 증가) | 1,119(50 증가) |
물질 | 농도 | 방출: 평균 | 방출: 표준편차 |
Triton X-100 | 3% 1% 0.5% 0.1% | 44027 45800 40834 19829 | 177 2888 39 103 |
SDS | 3% 1% 0.5% 0.1% | 62481 71809 76676 22990 | 180 1558 200 108 |
NaCl | 200mM 150mM 100mM 50mM | 68527 7622 6314 5680 | 2040 36 113 62 |
pH | 9 8 7 6 | 25265 18816 8781 7640 | 411 226 70 55 |
PEI의 농도(μM) | 0 | 1 | 10 | 50 | 100 |
생산량(%) | 89.0 | 92.3 | 91.0 | 87.5 | 86.3 |
PEI 농도 | 0 | 5μM | 10μM | 50μM | ||||
시간 | 평균 | 표준편차 | 평균 | 표준편차 | 평균 | 표준편차 | 평균 | 표준편차 |
2h | 6 | 0 | 49 | 4 | 67 | 7 | 116 | 6 |
4h | 7 | 3 | 63 | 5 | 89 | 9 | 159 | 10 |
6h | 6 | 0 | 65 | 10 | 94 | 13 | 203 | 12 |
24h | 9 | 3 | 120 | 5 | 129 | 3 | 291 | 17 |
48h | 6 | 1 | 160 | 18 | 171 | 13 | 306 | 6 |
시간 | 0 | 5 μM | 10μM | 50μM | PEI50 생존능 |
2h | 0.7 | 5.4 | 7.4 | 12.9 | 93.8% |
4h | 0.8 | 7.0 | 9.9 | 17.7 | 92.4% |
6h | 0.7 | 7.2 | 10.4 | 22.6 | 83.9% |
24h | 1.0 | 13.3 | 14.3 | 32.3 | 72.6% |
48h | 0.7 | 17.8 | 19.0 | 34.0 | 48.4% |
25 kDa PEI | 0 | 10μM | 50μM | 100μM |
총 단백질(㎍/mL) | 132.8 | 136.2 | 119.5 | 79.2 |
IL1(pg/mL) | 9.2 | 12.7 | 13.1 | 14.4 |
단백질 내 IL1(pg/mL) | 69.3 | 93.2 | 109.6 | 181.8 |
촉진지수 | 1 | 1.3 | 1.6 | 2.6 |
INCI 명칭 | 촉진지수 | 생존능 | 관찰여부 |
폴리에틸렌이민 25kDa | 34.7 | 74.1 | + |
코코디모니움 하이드록시프로필 가수분해된 밀 단백질 | 4.3 | 86 | - |
코코디모니움 하이드록시프로필 가수분해된 벼 단백질 | 18 | 85 | - |
스테아디모니움 하이드록시프로필 가수분해된 밀 단백질 | 4.6 | 86.4 | - |
로릴디모니움 하이드록시프로필 가수분해된 밀 단백질 | 6.2 | 87.5 | - |
하이드록시프로필트리모니움 가수분해된 밀 단백질 | 1.3 | 91.7 | - |
하이드록시프로필트리모니움 벌꿀(honey) | 15 | 92 | - |
소듐 라우로일 귀리 아미노산 | 0.8 | 76.6 | - |
소듐 라우로일 밀 아미노산 | 1.1 | 46.1 | - |
코코아민 | 32.7 | 79.7 | + |
라우릴디모니움 하이드록시프로필 가수분해된 대두 단백질 | 38.8 | 87.9 | + |
키토산 | 10.3 | 99 | - |
하이드록시프로필 구아 하이드록시프로필트리모니움 클로라이드 | 1.1 | 74.8 | - |
하이드록시프로필 구아 | -0.2 | 91.1 | - |
하이드록시프로필 구아 | -0.4 | 97.5 | - |
하이드록시프로필 구아 하이드록시프로필트리모니움 클로라이드 | 1.4 | 71.2 | - |
구아 하이드록시프로필트리모니움 | 0.6 | 53.3 | - |
메이프로 | 1 | 91.6 | - |
폴리쿼터니움 7 | 0.3 | 80.1 | - |
폴리비닐피롤리돈(1) | 1.4 | 85.1 | - |
폴리비닐카프로락탐 | 4.1 | 0 | - |
폴리비닐피롤리돈(2) | 0.7 | 26.6 | - |
폴리비닐피롤리돈(3) | 0.7 | 71 | - |
폴리쿼터니움 16(1) | 4.6 | 83.5 | - |
폴리쿼터니움 11(1) | 1.5 | 49.7 | - |
코코트리모니움 메토설페이트 | 0.1 | 55 | - |
폴리쿼터니움 16(2) | 8.4 | 33.8 | - |
폴리쿼터니움 16(3) | 1 | 38.8 | - |
폴리쿼터니움 16(4) | 12.5 | 67.1 | - |
폴리쿼터니움 16(5) | 0.2 | 85.3 | - |
폴리쿼터니움 44 | 0.8 | 59.7 | - |
코코알코니움 클로라이드 | 5.6 | 36.3 | - |
코코트리모니움 클로라이드 | -0.2 | 65.6 | - |
테트라하이드록시프로필 에틸렌디아민 | 1.9 | 95.3 | - |
스테라미도프로필 세테아릴 디모니움 토실레이트 및 PG | 13.1 | 93.2 | - |
쿼터니움 70 및 PG | -0.2 | 63.9 | - |
쿼터니움 26 | 30.9 | 59.2 | - |
쿼터니움 22 | 2 | 98.9 | - |
폴리코터니움 28 | 0.6 | 79.3 | - |
폴리쿼터니움 11(2) | 2.9 | 50.7 | - |
폴리쿼터니움 11(3) | 2.9 | 77.1 | - |
폴리쿼터니움 2 | 4.2 | 23.6 | - |
스테랄코니움 클로라이드 | 17.6 | 37.4 | - |
프로필아민 C3 | 0.9 | 103.3 | - |
n-부틸아민 C4 | 1.4 | 106.2 | - |
디부틸아민 2 C4 | 0.7 | 75.7 | - |
헥실아민 C6 | 0.2 | 82.1 | - |
헵틸아민 C7 | 3.7 | 39.4 | - |
디옥틸아민 2 C8 | 1 | 34.7 | - |
INCI 명칭 | 촉진지수 | 생존능 | 관찰 |
데실아민 C10 | 39.6 | 68.5 | + |
디데실아민 2 C10 | 1.2 | 28.3 | - |
운데실아민 C11 | 95.3 | 84 | + |
도데실아민 C12 | 47.1 | 57 | + |
트리데실아민 C13 | 44.5 | 62.6 | + |
테트라데실아민 C14 | 11.6 | 54.8 | - |
펜타데실아민 C15 | 14.9 | 73 | - |
옥타데실아민 C18 | 19.6 | 61.2 | - |
올레일아민 C18:1 | 1.9 | 87.1 | - |
1개의 알킬 지방사슬을 포함하는 1급 모노아민의 탄소 수 | 촉진지수 |
25 kDa PEI 대조군 | 34.7 |
C3 | 0.9 |
C4 | 1.4 |
C6 | 0.2 |
C7 | 3.7 |
C10 | 39.6 |
C11 | 95.3 |
C12 | 47.1 |
C13 | 44.5 |
C14 | 11.6 |
C15 | 14.9 |
C18 | 19.6 |
아민의 알킬 사슬의 수(사슬 길이) | 촉진지수 |
25 kDa PEI | 34.7 |
1(C4) | 1.7 |
2(C4) | 0.7 |
1(C10) | 39.6 |
2(C10) | 1.2 |
상품화된 4급화 물질 | 화학명 | 회사명 |
밀 | 코코디모니움, 스테아디모니움, 하이드록시프로필트리모니움 또는 로릴디모니움 가수분해된 밀 단백질, 밀 배아-아미도프로팔코니움 클로라이드 | Croda |
대두 | 로릴디모니움 하이드록시프로필 가수분해된 대두 단백질, 코코디모니움 하이드록시프로필 가수분해된 대두 단백질, 하이드록시프로필 트리메틸 암모늄 클로라이드 가수분해된 대두 단백질, 대두 디하이드록시프로필디모니움 글루코시드 | Croda RITA corporation |
케라틴 | 하이드록시프로필트리모니움 가수분해된 케라틴 | RITA corporation |
카제인 | 하이드록시프로필트리모니움 가수분해된 카제인 | RITA corporation |
콜라겐 | 하이드록시프로필트리모니움 가수분해된 콜라겐, 로릴디모니움 하이드록시프로필 가수분해된 콜라겐 | RITA corporation Cognis |
실크 | 하이드록시프로필트리모니움 가수분해된 실크 | RITA corporation |
벼 | 코코디모니움 하이드록시프로필 가수분해된 벼 단백질 | Sochibo |
구아 | 하이드록시프로필 구아 하이드록시프로필트리모니움 클로라이드, 하이드록시프로필 구아 하이드록시프로필트리모니움 클로라이드, 구아 하이드록시프로필트리모니움 | Meyhall Rhodia |
벌꿀 | 하이드록시프로필트리모니움 벌꿀(honey) | ARCH |
셀룰로우즈 | 폴리쿼터니움 4 및 10 폴리쿼터니움 39 | Quimasso |
4급화 대두(%) | 0.5 | 1 | 1.5 | 2 | 2.5 |
촉진지수 | 0.6 | 1.6 | 38.9 | 97.2 | 99.9 |
세포 생존능(%) | 92.4 | 97.9 | 87.9 | 75.4 | 77.3 |
기능성 물질의 농도 | 50μM PEI | 0.5% 대두 | 1% 대두 | 1.5% 대두 | 2% 대두 |
PNPP | 72.3 | 91.8 | 91.6 | 87.5 | 88.4 |
IL1 알파 | 350 | 137.5 | 137.5 | 212.5 | 187.5 |
IL1 알파/PNPP | 484.1 | 149.8 | 150.1 | 242.9 | 212.1 |
기능성 물질의 농도 | 50μM PEI | 0.5% 대두 | 1% 대두 | 1.5% 대두 | 2% 대두 |
PNPP | 59.8 | 91.8 | 91.6 | 87.5 | 88.5 |
카스파아제-1 | 642.8 | 76 | 87.7 | 78.3 | 117.5 |
카스파아제-1/PNPP | 1074.9 | 82.8 | 95.7 | 89.5 | 132.8 |
I | NI | A=I/NI | B=리포좀/대조군 | C=리포좀/자유형 | |
본 발명 물질 | 118990 | 58786 | 2.01 | 79.3% | +23% |
비관능화 리포좀 | 114907 | 52306 | 2.31 | 91.1% | +11% |
리포좀 PEI | 105257 | 40148 | 2.82 | 111.4% | -9% |
자유형 | 리포좀 | PEI 리포좀 | 대두 리포좀 | |
알부틴 | 0.004 | 0.001 | 0 | 0 |
Phytolight® | 0.01 | 0.008 | 0.003 | 0.0016 |
카테킨 | 0.007 | 0.007 | 0 | 0.003 |
자유형 | 리포좀 | 4급화 리포좀 | |
확산 | 0.57±0.03 | 1.17±0.05 | 1.76±0.13 |
방출 24h | 0.691±0.06 | 1.398±0.07 | 1.77±0.21 |
저장 | 0.81±0.1 | 1.27±0.17 | 2.61±0.33 |
Claims (31)
- 리포좀 조직 내의 일부분 이상에a) C10 내지 C13의 탄소-함유 사슬 길이의 1급, 2급, 3급 또는 4급 지방족 모노아민; 및b) 폴리쿼터늄 16, 4급화 벌꿀 중합체, 4급화 밀 단백질, 4급화 벼 단백질, 4급화 콩 단백질, 4급화 콜라겐, 4급화 케라틴, 4급화 카제인 및 4급화 셀룰로우즈로 구성된 군으로부터 선택되는 양이온성 중합체, 또는 양이온성 합성 중합체로 구성된 군으로부터 선택되는 물질 또는 물질들의 혼합물을 포함하는 활성 성분의 세포 내 침투를 촉진시키는 리포좀.
- 제 1항에 있어서, 상기 리포좀이 주름예방 활성, 항산화 활성, 슬리밍 활성, 피부 재생 활성, 피부 또는 모발 염색 활성을 위한 것임을 특징으로 하는 리포좀.
- 제 1항에 있어서, 상기 중합체가 폴리쿼터늄 16, 4급화 벌꿀 중합체, 4급화 밀 단백질, 4급화 벼 단백질, 4급화 콩 단백질, 4급화 콜라겐, 4급화 케라틴, 4급화 카제인 및 4급화 셀룰로우즈로 구성된 군으로부터 선택되는 것을 특징으로 하는 리포좀.
- 제 1항에 있어서, 상기 모노아민이 데실아민, 운데실아민, 도데실아민, 트리데실아민 및 C10 내지 C13의 탄화수소 사슬을 갖는 코프라(copra) 아민 혼합물로 구성된 군으로부터 선택되는 것임을 특징으로 하는 리포좀.
- 제 1항에 있어서, 상기 리포좀이, 리포좀 막을 변형시키는 1 종 이상의 작용제를 포함하는 지질상인 것을 특징으로 하는 리포좀.
- 제 5항에 있어서, 상기 작용제가 포스파티딜콜린, 레시틴, 포스파티딜에타놀아민, 세팔린, 포스파티딜세린, 포스파티딜글리세롤, 디포스파티딜글리세롤, 카디오리핀 및 포스파티딜이노시톨로 구성된 군에서 선택되는 극성 인지질 단독 또는 그것의 혼합물인 것을 특징으로 하는 리포좀.
- 제 5항에 있어서, 상기 작용제가 세라마이드, 스핑고포스포리피드 및 글리코스핑고리피드로 구성된 군에서 선택되는 극성 스핑고리피드 단독 또는 그것의 혼합물인 것을 특징으로 하는 리포좀.
- 제 6항에 있어서, 상기 리포좀이 대두, 포도, 해바라기, 루핀, 땅콩, 참깨, 서양호박, 브랜 오일(bran oil), 동백오일, 금잔화, 아마 및 대마로 구성된 군에서 선택되는 천연 재료 단독 또는 그것의 혼합물로부터 추출된 1 종 이상의 액상 레시틴을 포함하는 것을 특징으로 하는 리포좀.
- 제 5항에 있어서, 상기 리포좀이 지질상 내에 막을 견고하게 하는 작용제로서 액상 콜레스테롤 또는 콜레스테릴헤미석시네이트를 포함하는 것을 특징으로 하는 리포좀.
- 제 5항에 있어서, 상기 리포좀이 지질상 내에 리포좀 막을 유동화하는 작용제로서 1 종 이상의 계면활성제를 포함하는 것을 특징으로 하는 리포좀.
- 제 1항에 있어서, 상기 리포좀이 세포 내 침투 비활성인 형광물질 또는 형광성분을 포함함을 특징으로 하는 리포좀.
- 제 1항에 있어서, 상기 모노아민이 지방족 4급화 1급 모노아민 또는 지방족 4급 모노아민인 것을 특징으로 하는 리포좀.
- 제 1항에 있어서, 상기 모노아민이 4급화된 화학식 R-N(R1R2R3)(여기서, R은 가수분해되거나 혹은 그렇지 않은, 하이드록시알킬화된 식물 단백질을 나타내며, R1 및 R2는 각각 C1-C6 탄화수소기를 나타내고, R3는 10 내지 18 개의 탄소원자를 갖는 알킬 라디칼을 나타냄) 형태의 식물 단백질 용액으로부터 선택된 4급화된 1급 모노아민인 것을 특징으로 하는 리포좀.
- 제 13항에 있어서, 상기 R3가 12 개의 탄소원자를 갖는 라디칼(라우릴)인 것을 특징으로 하는 리포좀.
- 제 1항에 있어서, 상기 활성 성분이 리포좀 내에 존재하거나 보유된 것임을 특징으로 하는 리포좀.
- 제 15항에 있어서, 상기 활성 성분이 항-라디칼 작용제, 비타민 E, 플라보노이드, 카로티노이드, 비타민 C, 탈색 작용제, 카테킨, 하이드로퀴논, 아부틴, 파이트산(phytic acid), 엘라그산(ellagic acid), 비타민 C, 슬리밍제, 1 종 이상의 잔틴, 피부 또는 모발 염색제, 티로신, 트립토판, 페닐알라닌 및 콜레우스 추출물로 구성된 군으로부터 선택된 것임을 특징으로 하는 리포좀.
- 제 11항에 있어서, 상기 형광물질 또는 형광성분이 펜타플루오로벤조일아미노 플루오레신인 것을 특징으로 하는 리포좀.
- a) 리포좀내에 존재하거나 운반되는 1 종 이상의 활성 성분;b) 극성 인지질; 및c) 리포좀 조직내의 일부분 이상에서, 4급화 벌꿀 중합체, 4급화 밀 단백질, 4급화 쌀 단백질, 4급화 콩 단백질, 4급화 콜라겐, 4급화 케라틴, 4급화 카제인 및 4급화 셀룰로오스로 구성된 군으로 부터 선택되는 양이온성 천연 중합체 또는 천연 중합체 교부 양이온을 포함한 활성 성분의 세포 내 침투를 촉진시키는 물질 또는 이들의 혼합물을 포함하는 리포좀.
- 제1항 내지 제18항에서 정의된 리포좀 및 이 리포좀내에 존재하거나 운반되는 활성 성분을 미용적으로 허용가능한 부형제와의 혼합물로 포함하고, 상기 활성 성분이 항-라디칼 작용제, 비타민 E, 플라보노이드, 카로티노이드, 비타민 C, 탈색 작용제, 카테킨, 하이드로퀴논, 아부틴, 파이트산(phytic acid), 엘라그산(ellagic acid), 비타민 C, 슬리밍제, 1 종 이상의 잔틴, 피부 또는 모발 염색제, 티로신, 트립토판, 페닐알라닌 및 콜레우스 추출물로 구성된 군으로부터 선택되는 것을 특징으로 하는 미용 또는 피부미용 조성물.
- 제 19항에 있어서, 세포 내 침투를 촉진하는 물질의 농도는 최종 조성물의 중량당 0.05∼25%임을 특징으로 하는 미용 또는 피부미용 조성물.
- 제 19항에 있어서, 세포 내 침투를 촉진하는 물질의 농도는 최종 조성물의 중량당 0.5∼2.5%임을 특징으로 하는 미용 또는 피부미용 조성물.
- 삭제
- 주름예방활성, 항산화활성, 슬리밍 활성, 피부 미백 활성, 피부 혹은 모발 염색 활성을 갖는 제18항에 따른 리포좀을 포함하는 것을 특징으로 하는 미용 또는 피부미용 조성물.
- 제18항에서 정의된 리포좀 및 이 리포좀내에 존재하거나 운반되는 활성 성분을 포함하고, 상기 활성 성분이 항-라디칼 작용제, 비타민 E, 플라보노이드, 카로티노이드, 비타민 C, 탈색 작용제, 카테킨, 하이드로퀴논, 아부틴, 파이트산(phytic acid), 엘라그산(ellagic acid), 비타민 C, 슬리밍제, 1 종 이상의 잔틴, 피부 또는 모발 염색제, 티로신, 트립토판, 페닐알라닌 및 콜레우스 추출물로 구성된 군으로부터 선택되는 것을 특징으로 하는 미용 또는 피부미용 조성물.
- a) 제1항의 리포좀을 형성할 수 있는 물-지질 혼합물의 제조 단계;b) 상기 물-지질 혼합물에 형광 화합물 혼합시킨 후 분산시키는 단계;c) 상기 물-지질 혼합물에 세포 내 침투 촉진 활성을 스크리닝할 시험 물질 및 비교 물질을 혼합시킨 후 분산시키거나, 동시에 분산시키는 단계;d) 상기 b) 또는 c) 단계에서 얻은 물-지질 혼합물로부터 리포좀을 형성하는 방법에 따라 리포좀을 제조하는 단계; 및,e) 세포 내 형광도를 측정하여 형광 화합물의 세포 내 침투를 측정하는 단계를 포함하는 것을 특징으로 하는, 리포좀에 의해 운반되어 활성성분의 세포 내 침투를 촉진시키는 1 종 이상의 물질의 스크리닝 방법.
- a) 제18항의 리포좀을 형성할 수 있는 물-지질 혼합물의 제조 단계;b) 상기 물-지질 혼합물에 형광 화합물 혼합시킨 후 분산시키는 단계;c) 상기 물-지질 혼합물에 세포 내 침투 촉진 활성을 스크리닝할 시험 물질 및 비교 물질을 혼합시킨 후 분산시키거나, 동시에 분산시키는 단계;d) 상기 b) 또는 c) 단계에서 얻은 물-지질 혼합물로부터 리포좀을 형성하는 방법에 따라 리포좀을 제조하는 단계; 및,e) 세포 내 형광도를 측정하여 형광 화합물의 세포 내 침투를 측정하는 단계를 포함하는 것을 특징으로 하는 리포좀에 의해 운반되어 활성성분의 세포 내 침투를 촉진시키는 1 종 이상의 물질의 스크리닝 방법.
- 제 25항 또는 제 26항에 있어서, 형광 화합물의 세포내 침투 결과를 폴리에틸렌이민을 포함하는 비교 물질에서 얻은 세포내 투과도와 비교하는 것을 특징으로 하는 스크리닝 방법.
- 삭제
- 삭제
- 삭제
- 삭제
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- 2004-05-25 FR FR0405640A patent/FR2870741B1/fr not_active Expired - Lifetime
- 2004-06-30 US US10/880,810 patent/US9655822B2/en not_active Expired - Fee Related
- 2004-09-17 DE DE102004045186A patent/DE102004045186B9/de not_active Expired - Fee Related
- 2004-10-04 GB GB0422048A patent/GB2415375B/en not_active Expired - Fee Related
- 2004-12-10 KR KR1020040104333A patent/KR100697361B1/ko active IP Right Grant
- 2004-12-10 ES ES200402941A patent/ES2268946B2/es active Active
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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KR102223332B1 (ko) * | 2020-10-28 | 2021-03-08 | (주)캔디스피드코리아 | 리포좀 포장된 l-아르기닌 및 유기 지방산을 포함하는 염모제 조성물 |
Also Published As
Publication number | Publication date |
---|---|
DE102004045186B4 (de) | 2011-08-18 |
ES2268946A1 (es) | 2007-03-16 |
KR20050112498A (ko) | 2005-11-30 |
FR2870741A1 (fr) | 2005-12-02 |
JP5220546B2 (ja) | 2013-06-26 |
ES2268946B2 (es) | 2009-07-06 |
JP4950419B2 (ja) | 2012-06-13 |
JP2009108056A (ja) | 2009-05-21 |
FR2870741B1 (fr) | 2008-03-14 |
GB2415375B (en) | 2007-01-31 |
US9655822B2 (en) | 2017-05-23 |
DE102004045186A1 (de) | 2005-12-22 |
GB0422048D0 (en) | 2004-11-03 |
US20050266065A1 (en) | 2005-12-01 |
DE102004045186B9 (de) | 2012-02-16 |
JP2005350445A (ja) | 2005-12-22 |
GB2415375A (en) | 2005-12-28 |
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