KR960000234A - 메틸트리티오 항암제의 부형제-약물 컨쥬게이트, 이를 함유하는 제약학적 조성물 및 이의 제조 방법 - Google Patents
메틸트리티오 항암제의 부형제-약물 컨쥬게이트, 이를 함유하는 제약학적 조성물 및 이의 제조 방법 Download PDFInfo
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- KR960000234A KR960000234A KR1019950014699A KR19950014699A KR960000234A KR 960000234 A KR960000234 A KR 960000234A KR 1019950014699 A KR1019950014699 A KR 1019950014699A KR 19950014699 A KR19950014699 A KR 19950014699A KR 960000234 A KR960000234 A KR 960000234A
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- Prior art keywords
- conhr
- coor
- alk
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- 238000000034 method Methods 0.000 title claims abstract 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 5
- -1 Methyltrithio Chemical group 0.000 title claims 40
- 229940079593 drug Drugs 0.000 title abstract 3
- 239000003814 drug Substances 0.000 title abstract 3
- 239000002246 antineoplastic agent Substances 0.000 title 1
- 229930195731 calicheamicin Natural products 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract 36
- 230000002068 genetic effect Effects 0.000 claims abstract 7
- 239000000126 substance Substances 0.000 claims abstract 7
- 102000004169 proteins and genes Human genes 0.000 claims abstract 5
- 108090000623 proteins and genes Proteins 0.000 claims abstract 5
- 239000012634 fragment Substances 0.000 claims abstract 4
- 239000003102 growth factor Substances 0.000 claims abstract 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract 4
- HXCHCVDVKSCDHU-LULTVBGHSA-N calicheamicin Chemical compound C1[C@H](OC)[C@@H](NCC)CO[C@H]1O[C@H]1[C@H](O[C@@H]2C\3=C(NC(=O)OC)C(=O)C[C@](C/3=C/CSSSC)(O)C#C\C=C/C#C2)O[C@H](C)[C@@H](NO[C@@H]2O[C@H](C)[C@@H](SC(=O)C=3C(=C(OC)C(O[C@H]4[C@@H]([C@H](OC)[C@@H](O)[C@H](C)O4)O)=C(I)C=3C)OC)[C@@H](O)C2)[C@@H]1O HXCHCVDVKSCDHU-LULTVBGHSA-N 0.000 claims abstract 3
- 150000003431 steroids Chemical class 0.000 claims abstract 3
- 206010028980 Neoplasm Diseases 0.000 claims abstract 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000005309 thioalkoxy group Chemical group 0.000 claims 38
- 229910052736 halogen Inorganic materials 0.000 claims 37
- 150000002367 halogens Chemical class 0.000 claims 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 125000003545 alkoxy group Chemical group 0.000 claims 21
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 18
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 15
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 12
- 229940127089 cytotoxic agent Drugs 0.000 claims 12
- 239000002254 cytotoxic agent Substances 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 150000003254 radicals Chemical class 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 150000002431 hydrogen Chemical group 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 4
- 150000001450 anions Chemical class 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 229950000688 phenothiazine Drugs 0.000 claims 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 4
- 125000005208 trialkylammonium group Chemical group 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 3
- 125000006715 (C1-C5) alkylthio group Chemical group 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 3
- 239000012190 activator Substances 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 239000012062 aqueous buffer Substances 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 239000011630 iodine Substances 0.000 claims 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 3
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000005493 quinolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 2
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 claims 2
- PBYIIRLNRCVTMQ-UHFFFAOYSA-N 2,3,5,6-tetrafluorophenol Chemical compound OC1=C(F)C(F)=CC(F)=C1F PBYIIRLNRCVTMQ-UHFFFAOYSA-N 0.000 claims 2
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 claims 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 2
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims 2
- DMGNFLJBACZMRM-UHFFFAOYSA-N O[P] Chemical class O[P] DMGNFLJBACZMRM-UHFFFAOYSA-N 0.000 claims 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 239000007822 coupling agent Substances 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 238000007911 parenteral administration Methods 0.000 claims 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims 2
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HOGDNTQCSIKEEV-UHFFFAOYSA-N n'-hydroxybutanediamide Chemical compound NC(=O)CCC(=O)NO HOGDNTQCSIKEEV-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000012064 sodium phosphate buffer Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- 230000001093 anti-cancer Effects 0.000 abstract 2
- 229940088710 antibiotic agent Drugs 0.000 abstract 2
- 230000035755 proliferation Effects 0.000 abstract 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 abstract 1
- 229930189413 Esperamicin Natural products 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- LJQQFQHBKUKHIS-WJHRIEJJSA-N esperamicin Chemical compound O1CC(NC(C)C)C(OC)CC1OC1C(O)C(NOC2OC(C)C(SC)C(O)C2)C(C)OC1OC1C(\C2=C/CSSSC)=C(NC(=O)OC)C(=O)C(OC3OC(C)C(O)C(OC(=O)C=4C(=CC(OC)=C(OC)C=4)NC(=O)C(=C)OC)C3)C2(O)C#C\C=C/C#C1 LJQQFQHBKUKHIS-WJHRIEJJSA-N 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 230000008685 targeting Effects 0.000 abstract 1
- OYNIIKHNXNPSAG-UHFFFAOYSA-N 2-(4-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C=O)C=C1 OYNIIKHNXNPSAG-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
- A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
- A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
- A61K47/6807—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug or compound being a sugar, nucleoside, nucleotide, nucleic acid, e.g. RNA antisense
- A61K47/6809—Antibiotics, e.g. antitumor antibiotics anthracyclins, adriamycin, doxorubicin or daunomycin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Life Sciences & Earth Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Abstract
본 발명은 칼리케아미신종의 유효 항암 항생제 및 그 유도체의 이황화물 동족체, 및 에스페르아미신과 같은 관련 항암 항생제로부터 유사 동족체로부터 제조된 부형제-약물 컨쥬게이트(conjugate)를 기재한다. 상기 부형제는 종양의 증식과 같은 바람직하지 않은 세포의 증식을 타겟하는 항체, 성장 인자 또는 스테로이드일 수 있다. 단백질 부형제 전체 뿐 아니라 그의 항원-인식 단편 및 그의 화학적 또는 유전학적 처리 대응부가 컨쥬게이트의 타겟팅 부분으로 이용될 수 있다. 본 발명은 상기 컨쥬게이트의 합성에 요구되는 화합물, 부형제-약물 컨쥬게이트의 적당한 제약학적 조성물 및 그의 사용 방법을 포함한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제Ⅰ도는 칼리케아미신 N-아세틸 감마 디메틸 히드라지드와 축합된 4-포르밀페녹시아세트산의 양성자 자기 공명 스펙트럼을 나타낸다.
Claims (44)
- 하기 일반식의 세포독성 약물 컨쥬게이트(conjugate):Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]m상기 식에서 Z3는 모노-및 폴리클로날 항체, 그의 항원-인식 단편 및 그의 화학적 또는 유전학적 처리 대응부, 및 성장 인자 및 그의 화학적 또는 유전학적 처리 대응부로부터 선택된 단백질(이때, 단백질에 대한 공유 결합은 "m" 라이신 측쇄와의 반응으로부터 형성된 아미드임), 또는 스테로이드(이때, 스테로이드에 대한 공유 결합은 아미드 또는 에스테르임)이고; Alk1및 Alk2는 각각 결합이거나, 분지 또는 미분지(C1-C10)알킬렌 연쇄이고; Sp1은 결합, -S-, -O-, -CONH-, -NHCO-, -NR'-, N(CH2CH2)2N-, 또는 -X- Ar'-Y-(CH2)n-Z로서, 이때 X, Y 및 Z는 각각 결합, -NR'-, -S-, 또는 -O-이며, 단 n=0이면 Y 및 Z중 적어도 하나는 결합이어야 하고 Ar'은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'중 1, 2 또는 3개의 기로 임의로 치환된 1,2-, 1,3-, 또는 1,4- 페닐렌이며, 단 Alk1이 결합일때 Sp1이 결합이고; n은 0-5의 정수이고; R'은 -OH, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, (C1-C3) 디알킬아미노, 또는 (C1-C3)트리알킬암모늄 -A-(이때, A-는 염을 이루는 제약학적 허용가능 음이온임)중 1 또는 2개의 기로 임의로 치환된 분지 또는 비분지(C1-C5) 연쇄이고; Ar은 (C1-C6)알킬 (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR, S(CH2)nCOOR', O(CH2)nCONHR' 또는 S(CH2)nCONHR', (이때, n 및 R'은 상기 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 1,2-, 1,3- 또는 1,4-페닐렌이거나, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, 또는 2,7-나프틸리덴 또는으로서, (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR' (이때, n 및 R'은 상기 정의된 바와 같음)중 1,2,3 또는 4개의 기로 임의로 치환된 각각의 나프틸리덴 또는 페노티아진이며, 단 Ar이 나프틸리덴이면 Z'은 수소가 아니고, 단 Ar이 페노타아진이면 Sp1은 질소에만 연결된 결합이고; SP2는 결합, -S-, 또는 -O-이며, 단 Alk2가 결합일때 Sp2가 결합이고; Z1은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR', (이때, n 및 R'은 상기 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 페닐, (C1-C5)알킬 또는 H이고; Z2는 Q-Sp-SS-W이며, 이때 W는으로서,R1은또는 CH3이고; R2는또는 H이고;R3은또는 H이고; R4는또는 H이고;R6또는 R7은 H이거나이고;R5는 -CH3, -C2H5, 또는 -CH(CH3)2이고; X는 요오드 또는 브롬 원자이고; R5'는 수소 또는 RCO기로서, 이때 R은 수소, 분지 또는 비분지(C1-C10)알킬 또는 (C1-C10)알킬렌기, (C6-C11)아릴기, (C6-C11)아릴-알킬 (C1-C5)기, 또는 헤테로아릴 또는 헤테로아릴-알킬 (C1-C5)기(여기서 헤테로아릴은 2-, 또는 3-푸릴, 2- 또는 3-티에닐, 2- 또는 3-(N-메틸피롤릴), 2-, 3-, 또는 4- 피리딜, 2-, 4-, 또는 5-(N-메틸이미다졸릴), 2-, 4-, 또는 5-옥사졸릴, 2-, 3-, 5-, 또는 6-피리미디닐, 2-, 3-, 4-, 5-, 6-, 7-, 또는 9-퀴놀릴, 또는 1-, 3-, 4-, 5-, 6-, 7-, 또는 8-이소퀴놀릴임)로서, 이때 모든 아릴 및 헤테로아릴기는 히드록시, 아미노, 카르복시, 할로, 니트로, 저급 (C1-C3)알콕시, 또는 저급 (C1-C5)티오알콕시기 하나 이상에 의해 임의로 치환되고; Sp는 직쇄 또는 분지쇄 이가 또는 삼가 (C1-C18)라디칼, 이가 또는 삼가 아릴 또는 헤테로아릴 라디칼, 이가 또는 삼가 (C3-C18)시클로알킬 또는 헤테로시클로알킬 라디칼, 이가 또는 삼가 아릴- 또는 헤테로아릴-알킬 (C1-C18)라디칼, 이가 또는 삼가 시클로알킬- 또는 헤테로시클로알킬- 알킬 (C1-C18)라디칼, 또는 이가 또는 삼가 (C2-C18)불포화 알킬 라디칼이며, 이때 헤테로아릴은 푸릴, 티에닐, N-메틸피롤릴, 피리디닐, N-메틸이미다졸릴, 옥사졸릴, 피리미디닐, 퀴놀릴, 이소퀴놀릴, N-메틸카르바조일, 아미노쿠마리닐, 또는 페나지닐이며, 이때 Sp가 삼가 라디칼이면 Sp는 저급 (C1-C5)디알킬아미노, 저급 (C1-C5)알콕시, 히드록시 또는 저급 (C1-C5)알킬티오기에 의해 임의로 치환될 수 있고; Q는 =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, 또는 =NHO-이고, m은 약 0.1-15의 정수이다.
- 제1항에 있어서, Alk2는 분지 또는 비분지 (C1-C10)알킬렌 연쇄이고, Z1은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제1항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 페닐인 세포독성 약물 컨쥬게이트.
- 제1항에 있어서, Alk2는 분지 또는 비분지 (C1-C10)알킬렌 연쇄이고, Z1은 H 또는 (C1-C5)알킬인 세포독성 약물 컨쥬게이트.
- 제1항에 있어서, Alk2및 Sp2는 함께 결합이고, Z1은 H 또는 (C1-C5)알킬인 세포독성 약물.
- 제1항에 있어서, Alk2는 및 Sp2는 함께 결합이고, Z1은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제1항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 페닐인 세포독성 약물 컨쥬게이트.
- 제2, 3, 4 또는 5항에 있어서, Sp1는 결합, -S-, -O-, -CONH-, -NHCO-, 또는 -NR'으로서, 이때 n 및 R'은 제1항에 정의된 바와 같으며, 단 Alk1이 결합일때 Sp1이 결합인 세포독성 약물 컨쥬게이트.
- 제6항에 있어서, Ar은 (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제1항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 1,2-, 1,3-, 또는 1,4-페닐렌이거나, Ar은 각각 (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제1항에 정의된 바와 같음)으로 임의로 치환된 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, 또는 2,7-나프틸리덴인 세포독성 약물 컨쥬게이트.
- 제7항에 있어서, Z3는 모노- 및 폴리클로날 항체, 그의 항원-인식 단편, 및 그의 화학적 또는 유전학적 처리 대응부, 및 성장인자 및 그의 화학적 또는 유전학적 처리 대응부로부터 선택된 단백질(이때, 단백질에 대한 공유 결합은 "m" 라이신 측쇄와의 반응으로부터 형성된 아미드임)인 세포독성 약물 컨쥬게이트.
- 제8항에 있어서, Z2는 Q-Sp-SS-W이고, 이때 W는으로서,R1는이고; R2는또는 H이고;R4는또는 H이고;R5, X, R5', R, 및 Sp는 제1항에 정의된 바와 같고; Q는 =NHNCO-인 세포독성 약물 컨쥬게이트.
- 제9항에 있어서, Ar은 (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제1항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 1,2-, 1,3-, 또는 1,4-페닐렌이고, Alk2와 Sp2는 함께 결합이고, Z1은 H 또는 (C1-C5)알킬인 세포독성 약물 컨쥬게이트.
- 제10항에 있어서, Sp1은 -O-이고, Alk1은 C4알킬이고, Ar은 1,4-페닐렌이고, Z1은 C1알킬인 세포독성 약물 컨쥬게이트.
- 제11항에 있어서, Z3는 항체 h- 또는 m-P67.6, h- 또는 m-CT-M-01, h- 또는 m-A33, 또는 항체-Tac이고, Z2는 칼리케아미신 감마 디메틸 히드라지드 또는 칼리케아미신 N-아세틸 감마 디메틸 히드라지드인 세포독성 약물 컨쥬게이트.
- 제12항에 있어서, Z3는 항체 h-CT-M-01이고, Z2는 칼리케아미신 N-아세틸 감마 디메틸 히드라지드인 세포독성 약물 컨쥬게이트.
- 제12항에 있어서, Z3는 항체 h-P67.6이고, Z2는 칼리케아미신 N-아세틸 감마 디메틸 히드라지드인 세포독성 약물 컨쥬게이트.
- 하기 일반식의 화합물로서:Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]mZ3는 할로겐, 히드록시, OM(이때 M은 염을 이루는 금속임), -N3,, 또는이고;Alk1및 Alk2는 각각 결합이거나, 분지 또는 비분지(C1-C10)알킬렌 연쇄이고; Sp1은 결합, -S-, -O-, -CONH-, -NHCO-, -NR'-, N(CH2CH2)2N-, 또는 -X-Ar'-Y-(CH2)n-Z로서, 이때 X, Y 및 Z는 각각 결합, -NR'-, -S-, 또는 -O-이며, 단 n=0이면 Y 및 Z중 적어도 하나는 결합이어야 하고 Ar'은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'중 1, 2 또는 3개의 기로 임의로 치환된 1,2-, 1,3-, 또는 1,4- 페닐렌이거나 Alk1이 결합일때 Sp1이 결합이고; n은 0-5의 정수이고; R'은 -OH, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, (C1-C3) 디알킬아미노, 또는 (C1-C3)트리알킬암모늄 -A-(이때, A-는 염을 이루는 제약학적 허용가능 음이온임)중 1 또는 2개의 기로 임의로 치환된 분지 또는 비분지(C1-C5) 연쇄이고; Ar은 (C1-C6)알킬 (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR, S(CH2)nCOOR', O(CH2)nCONHR' 또는 S(CH2)nCONHR', (이때, n 및 R'은 제1항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 1,2-, 1,3- 또는 1,4-페닐렌이거나, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, 또는 2,7-나프틸리덴 또는으로서, (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR' (이때, n 및 R'은 제1항에 정의된 바와 같음)중 1,2,3 또는 4개의 기로 임의로 치환된 각각의 나프틸리덴 또는 페노티아진이며, 단 Ar이 나프틸리덴이면 Z'은 수소가 아니고, 단 Ar이 페노타아진이면 Sp1은 질소에만 연결된 결합이고; SP2는 결합, -S-, 또는 -O-이며, 단 Alk2가 결합일때 Sp2가 결합이고; Z1은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR', (이때, n 및 R'은 상기 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 페닐, (C1-C5)알킬 또는 H이고; Z2는 Q-Sp-SS-W이며, 이때 W는으로서,R1은또는 CH3이고; R2는또는 H이고;R3은또는 H이고; R4는또는 H이고;R6또는 R7은 H 또는이고;R5는 -CH3, -C2H5, 또는 -CH(CH3)2이고; X는 요오드 또는 브롬 원자이고; R5'는 수소 또는 RCO기로서, 이때 R은 수소, 분지 또는 비분지(C1-C10)알킬 또는 (C1-C10)알킬렌기, (C6-C11)아릴기, (C6-C11)아릴-알킬 (C1-C5)기, 또는 헤테로아릴 또는 헤테로아릴-알킬 (C1-C5)기(여기서 헤테로아릴은 2-, 또는 3-푸릴, 2- 또는 3-티에닐, 2- 또는 3-(N-메틸피롤릴), 2-, 3-, 또는 4- 피리딜, 2-, 4-, 또는 5-(N-메틸이미다졸릴), 2-, 4-, 또는 5-옥사졸릴, 2-, 3-, 5-, 또는 6-피리미디닐, 2-, 3-, 4-, 5-, 6-, 7-, 또는 8-퀴놀릴, 또는 1-, 3-, 4-, 5-, 6-, 7-, 또는 8-이소퀴놀릴임)로서, 이때 모든 아릴 및 헤테로아릴기는 히드록시, 아미노, 카르복시, 할로, 니트로, 저급 (C1-C3)알콕시, 또는 저급 (C1-C5)티오알콕시기 하나 이상에 의해 임의로 치환되고; Sp는 직쇄 또는 분지쇄 이가 또는 삼가 (C1-C18)라디칼, 이가 또는 삼가 아릴 또는 헤테로아릴 라디칼, 이가 또는 삼가 (C3-C18)시클로알킬 또는 헤테로시클로알킬 라디칼, 이가 또는 삼가 아릴- 또는 헤테로아릴-알킬 (C1-C18)라디칼, 이가 또는 삼가 시클로알킬- 또는 헤테로시클로알킬- 알킬 (C1-C18)라디칼, 또는 이가 또는 삼가 (C2-C18)불포화 알킬 라디칼이며, 이때 헤테로아릴은 푸릴, 티에닐, N-메틸피롤릴, 피리디닐, N-메틸이미다졸릴, 옥사졸릴, 피리미디닐, 퀴놀릴, 이소퀴놀릴, N-메틸카르바조일, 아미노쿠마리닐, 또는 페나지닐이며, 이때 Sp가 삼가 라디칼이면 Sp는 저급 (C1-C5)디알킬아미노, 저급 (C1-C5)알콕시, 히드록시 또는 저급 (C1-C5)알킬티오기에 의해 임의로 치환될 수 있고; Q는 =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, 또는 =NHO-이고, m은 약 1인 화합물.
- 제15항에 있어서, Z3는 히드록시,인 화합물.
- 제16항에 있어서, Alk2는 분지 또는 비분지 (C1-C10)알킬렌 연쇄이고, Z1은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제1항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 페닐인 화합물.
- 제17항에 있어서, Alk2는 분지 또는 비분지 (C1-C10)알킬렌 연쇄이고, Z1은 H 또는 (C1-C5)알킬인 화합물.
- 제18항에 있어서, Alk2및 Sp2는 함께 결합이고, Z1은 H 또는 (C1-C5)알킬인 화합물.
- 제19항에 있어서, Alk2는 및 Sp2는 함께 결합이고, Z1은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제1항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 페닐인 화합물.
- 제17, 18, 19 또는 20항에 있어서, Sp1는 결합, -S-, -O-, -CONH-, -NHCO-, 또는 -NR'이고, 이때 R'은 상기 정의된 바와 같으며, 단 Alk1이 결합일면 Sp1이 결합인 화합물.
- 제21항에 있어서, Ar은 (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제1항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 1,2-, 1,3-, 또는 1,4-페닐렌이거나, 각각 (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제1항에 정의된 바와 같음)중 1, 2, 3 또는 4개의 기로 임의로 치환된 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, 또는 2,7-나프틸리덴인 화합물.
- 제22항에 있어서, Z2는 Q-Sp-SS-W이고, 이때 W는으로서,R1는이고; R2는또는 H이고;R4는또는 H이고;R5, X, R5', R, 및 Sp는 제1항에 정의된 바와 같고; Q는 =NHNCO-인 화합물.
- 제23항에 있어서, Alk2및 Sp2는 함께 결합이고, Ar은 (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제1항에 정의된 바와 같음)이고, Z1이 H 또는 (C1-C5)알킬인 화합물.
- 제24항에 있어서, Sp1은 -O-이고, Alk1은 C4알킬이고, Ar은 1,4-페닐렌이고, Z1은 C1알킬인 화합물.
- 제25항에 있어서, Z2는 칼리케아미신 감마 디메틸 히드라지드 또는 칼리케아미신 N-아세틸 감마 디메틸 히드라지드인 화합물.
- 하기 일반식의 화합물로서:Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]mZ3는 할로겐, 히드록시, OM(이때 M은 염을 이루는 금속임), -N3,, 또는이고;Alk1및 Alk2는 각각 결합이거나, 분지 또는 비분지(C1-C10)알킬렌 연쇄이고; Sp1은 결합, -S-, -O-, -CONH-, -NHCO-, -NR'-, N(CH2CH2)2N-, 또는 -X-Ar'-Y-(CH2)n-Z로서, 이때 X, Y 및 Z는 각각 결합, -NR'-, -S-, 또는 -O-이며, 단 n=0이면 Y 및 Z중 적어도 하나는 결합이어야 하고 Ar'은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'중 1, 2 또는 3개의 기로 임의로 치환된 1,2-, 1,3-, 또는 1,4- 페닐렌이거나 Alk1이 결합일때 Sp1이 결합이고; n은 0-5의 정수이고; R'은 -OH, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, (C1-C3) 디알킬아미노, 또는 (C1-C3)트리알킬암모늄 -A-(이때, A-는 염을 이루는 제약학적 허용가능 음이온임)중 1 또는 2개의 기로 임의로 치환된 분지 또는 비분지(C1-C5) 연쇄이고; Ar은 (C1-C6)알킬 (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR, S(CH2)nCOOR', O(CH2)nCONHR' 또는 S(CH2)nCONHR', (이때, n 및 R'은 상기 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 1,2-, 1,3- 또는 1,4-페닐렌이거나, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, 또는 2,7-나프틸리덴 또는으로서, (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR' (이때, n 및 R'은 상기 정의된 바와 같음)중 1,2,3 또는 4개의 기로 임의로 치환된 각각의 나프틸리덴 또는 페노티아진이며, 단 Ar이 나프틸리덴이면 Z1은 수소가 아니고, 단 Ar이 페노타아진이면 Sp1은 질소에만 연결된 결합이고; SP2는 결합, -S-, 또는 -O-이며, 단 Alk2가 결합일때 Sp2가 결합이고; Z1은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR', (이때, n 및 R'은 제1항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 페닐, (C1-C5)알킬 또는 H이고; Z2는 산소이고; m은 1이며, 단 Ar이 비치환 2,6-나프틸렌이거나, (C1-C6)알킬 또는 (C1-C5)알콕시 중 1개의 기로 임의로 치환된 1,3- 또는 1,4-페닐렌이고, Alk2가 결합이면 Sp1은 결합, -O-, 또는 -NHCO-가 아닌 화합물.
- 제27항에 있어서, Z3는 히드록시,인 화합물.
- 제28항에 있어서, Alk2는 분지 또는 비분지 (C1-C10)알킬렌 연쇄이고, Z1은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제27항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 페닐인 화합물.
- 제28항에 있어서, Alk2는 분지 또는 비분지 (C1-C10)알킬렌 연쇄이고, Z1은 H 또는 (C1-C5)알킬인 화합물.
- 제28항에 있어서, Alk2및 Sp2는 함께 결합이고, Z1은 H 또는 (C1-C5)알킬인 화합물.
- 제28항에 있어서, Alk2는 및 Sp2는 함께 결합이고, Z1은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제27항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 페닐인 화합물.
- 제29, 30, 31 또는 32항에 있어서, Sp1는 결합, -S-, -O-, -CONH-, -NHCO-, 또는 -NR'이고, 이때 R'은 상기 정의된 바와 같으며, 단 Alk1이 결합일때 Sp1이 결합인 화합물.
- 제33항에 있어서, Ar은 (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제27항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 1,2-, 1,3-, 또는 1,4-페닐렌이거나, 각각 (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제27항에 정의된 바와 같음)중 1, 2, 3 또는 4개의 기로 임의로 치환된 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, 또는 2,7-나프틸리덴인 화합물.
- 제34항에 있어서, Alk2및 Sp2는 함께 결합이고, Ar은 (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'(이때 n 및 R'은 제27항에 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 1,2-, 1,3-, 또는 1,4-페닐렌이거나, Z1은 H 또는 (C1-C5)알킬인 화합물.
- 제1항의 컨쥬게이트 및 비경구-투여 매질로 구성되는 제약학적 조성물.
- 제13 또는 14항의 컨쥬게이트 및 비경구-투여 매질로 구성되는 제약학적 조성물.
- 제1항의 컨쥬게이트를 환자에게 투여하는 것으로 구성되는, 바람직하지 않은 세포의 성장을 제어하는 방법.
- 제13 또는 14항의 컨쥬게이트를 환자에게 투여하는 것으로 구성되는, 바람직하지 않은 세포의 성장을 제어하는 방법.
- 제45 또는 46항에 있어서, 바람직하지 않은 세포가 포유류내 암세포인 방법.
- 약 100mM 염화 나트륨 및 약 100mM 수크로스를 함유하는 pH 약 7.4의 약 5mM 인산 나트륨 완충액내에 용해된 컨쥬게이트 약 1㎎/㎖ 용액을 동결-건조시켜 얻는, 제13 또는 14항의 컨쥬게이트를 포함하는 동결-건조 제약학적 조성물.
- 타겟된 유도체 Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]m의 제조 방법으로서, 일반식 Z2화합물중 이때 Z2는 Q-Sp-SS-W이고 W는으로서,R1은또는 CH3이고; R2는또는 H이고;R3은또는 H이고; R4는또는 H이고;R6또는 R7은 H 또는이고;R5는 -CH3, -C2H5, 또는 -CH(CH3)2이고; X는 요오드 또는 브롬 원자이고; R5'는 수소 또는 RCO기로서, 이때 R은 수소, 분지 또는 비분지(C1-C10)알킬 또는 (C1-C10)알킬렌기, (C6-C11)아릴기, (C6-C11)아릴-알킬 (C1-C5)기, 또는 헤테로아릴 또는 헤테로아릴-알킬 (C1-C5)기(여기서 헤테로아릴은 2-, 또는 3-푸릴, 2- 또는 3-티에닐, 2- 또는 3-(N-메틸피롤릴), 2-, 3-, 또는 4- 피리딜, 2-, 4-, 또는 5-(N-메틸이미다졸릴), 2-, 4-, 또는 5-옥사졸릴, 2-, 3-, 5-, 또는 6-피리미디닐, 2-, 3-, 4-, 5-, 6-, 7-, 또는 8-퀴놀릴, 또는 1-, 3-, 4-, 5-, 6-, 7-, 또는 8-이소퀴놀릴임)로서, 이때 모든 아릴 및 헤테로아릴기는 히드록시, 아미노, 카르복시, 할로, 니트로, 저급 (C1-C3)알콕시, 또는 저급 (C1-C5)티오알콕시기 하나 이상으로 임의로 치환되고; Sp는 직쇄 또는 분지쇄 이가 또는 삼가 (C1-C18)라디칼, 이가 또는 삼가 아릴 또는 헤테로아릴 라디칼, 이가 또는 삼가 (C3-C18)시클로알킬 또는 헤테로시클로알킬 라디칼, 이가 또는 삼가 아릴- 또는 헤테로아릴-알킬 (C1-C18)라디칼, 이가 또는 삼가 시클로알킬- 또는 헤테로시클로알킬- 알킬 (C1-C18)라디칼, 또는 이가 또는 삼가 (C2-C18)불포화 알킬 라디칼이며, 이때 헤테로아릴은 푸릴, 티에닐, N-메틸피롤릴, 피리디닐, N-메틸이미다졸릴, 옥사졸릴, 피리미디닐, 퀴놀릴, 이소퀴놀릴, N-메틸카르바조일, 아미노쿠마리닐, 또는 페나지닐이며, 이때 Sp가 삼가 라디칼이면 Sp는 저급 (C1-C5)디알킬아미노, 저급 (C1-C5)알콕시, 히드록시 또는 저급 (C1-C5)알킬티오기에 의해 임의로 치환될 수 있고; Q는 =H2NHNCO-, =H2NHNCS-, =H2NHNCONH-, =NHNCSNH-, 또는 =H2NO-임)으로서, Z2를 하기 일반식의 화합물:HOCO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=O(이때 Alk1및 Alk2는 각각 결합이거나, 분지 또는 비분지(C1-C10)알킬렌 연쇄이고; Sp1은 결합, -S-, -O-, -CONH-, -NHCO-, -NR'-, N(CH2CH2)2N-, 또는 -X-Ar'-Y-(CH2)n-Z로서, 이때 X, Y 및 Z는 각각 결합, -NR'-, -S-, 또는 -O-이며, 단 n=0이면 Y 및 Z중 적어도 하나는 결합이어야 하고 Ar'은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR'중 1, 2 또는 3개의 기로 임의로 치환된 1,2-, 1,3-, 또는 1,4- 페닐렌이며, 단 Alk1이 결합일때 Sp1이 결합이고; n은 0-5의 정수이고; R'은 -OH, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, (C1-C3) 디알킬아미노, 또는 (C1-C3)트리알킬암모늄 -A-(이때, A-는 염을 이루는 제약학적 허용가능 음이온임)중 1 또는 2개의 기로 임의로 치환된 분지 또는 비분지(C1-C5) 연쇄이고; Sp2가 결합이고; Z1은 (C1-C5)알킬, (C1-C4)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, COOR', CONHR', O(CH2)nCOOR, S(CH2)nCOOR', O(CH2)nCONHR' 또는 S(CH2)nCONHR', (이때, n 및 R'은 상기 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 페닐, (C1-C5)알킬 또는 H이고; Ar은 (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR, S(CH2)nCOOR', O(CH2)nCONHR' 또는 S(CH2)nCONHR'(이때, n 및 R'은 상기 정의된 바와 같음)중 1,2 또는 3개의 기로 임의로 치환된 1,2-, 1,3- 또는 1,4-페닐렌이거나, 1,2-, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 1,8-, 2,3-, 2,6-, 또는 2,7-나프틸리덴 또는으로서, (C1-C6)알킬, (C1-C5)알콕시, (C1-C4)티오알콕시, 할로겐, 니트로, 또는 COOR', CONHR', O(CH2)nCOOR', S(CH2)nCOOR', O(CH2)nCONHR', 또는 S(CH2)nCONHR' (이때, n 및 R'은 상기 정의된 바와 같음)중 1,2,3 또는 4개의 기로 임의로 치환된 각각의 나프틸리덴 또는 페노티아진이며, 단 Ar이 나프틸리덴이면 Z1은 수소가 아니고, 단 Ar이 페노타아진이면 Sp1은 질소에만 연결된 결합임)과 약 100℃ 이하의 끓는 점을 갖는 알콜성 용매내에서 약 20°-70℃에서 약 5% 아세트산 또는 다른 유사한 산 촉매의 존재하에 약 1-24시간 반응시키고, 하기 일반식의 중간체:HOCO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2(상기 식에서, Alk1, Sp1, Ar, Sp2, Alk2, 및 Z1은 상기 정의된 바와 같고; Z2는 Q-Sp-SS-W이며, 이때 Sp 및 W는 상기 정의된 바와 같고; Q는 =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, 또는 =NO-임)를 단리한 후, 하기 일반식의 화합물:HOCO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2을 N- 히드록시숙신아미드, 2,3,5,6-테트라플루오로페놀, 펜타플루오로페놀, 4-니트로페놀, 2,4-디니트로페놀, 또는 다른 적합한 활성화기와 함께 DCC, EDCI 또는 다른 커플링제의 존재하에 아세토니트릴 또는 5-50% DMF 함유 아세토니트릴과 같은 불활성 유기 용매내에서 반응시켜 하기 화합물:Z'3CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2(상기 식에서, Alk1, Sp1, Ar, Sp2, Alk2, 및 Z1은 상기 정의된 바와 같고; Z2는 Q-Sp-SS-W이며, 이때 Sp 및 W는 상기 정의된 바와 같고; Q는 =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, 또는 =NO-이고; Z3'은, 또는이고;또는 다른 비견할만한 산 활성화기임)을 생성하고, 최종적으로 하기 화합물:Z'3CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2을 부형제 Z3(이때, Z3는 모노- 및 폴리클로날 항체, 그의 항원-인식 단편 및 그의 화학적 또는 유전학적 처리 대응부, 및 성장인자 및 그의 화학적 또는 유전학적 처리 대응부임)과 함께 pH 6.5-9.0 및 4°-40℃온도의 수성 완충액내에서 1-48시간 반응시켜 하기 일반식의 화합물:Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]m(상기 식에서, Alk1, Sp1, Ar, Sp2, Alk2, Z1및 Z3은 상기 정의된 바와 같고; Z2는 Q-Sp-SS-W이며, 이때 Sp 및 W는 상기 정의된 바와 같고; Q는 =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, 또는 =NO-이고; m은 약 0.1-15의 정수임)을 생성하거나, 하기 일반식의 화합물:HOCO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=O(상기 식에서, Alk1, Sp1, Ar, Sp2, Alk2는 상기 정의된 바와 같음)을 N-히드록시숙신이미드, 2,3,5,6-테트라플루오로페놀, 펜타플루오로페놀, 4-니트로페놀, 2,4-디니트로페놀, 다른 적합한 활성화기와 함께 DCC, EDCI, 또는 다른 커플링제의 존재하에 아세토니트릴, 또는 5-50% DMF 함유 아세토니트릴과 같은 불활성 유기 용매내에서 반응시켜 하기 일반식의 화합물:Z3'CO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=O(상기 식에서, Alk1, Sp1, Ar, Sp2, Alk2및 Z3는 상기 정의된 바와 같음)을 생성한 후, 하기 화합물:Z3'CO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=O을 부형제 Z3(이때, Z3는 상기 정의된 바와 같음)와 함께 pH 6.5-9.0 및 4°-40℃ 온도의 수성 완충액내에서 1-48시간 동안 반응시켜 하기 일반식의 화합물:Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=O]m(상기 식에서, Alk1, Sp1, Ar, Sp2, Alk2, Z3및 m은 상기 정의된 바와 같음)을 생성하고, 최종적으로 하기 화합물 Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=O]m을 일반식 Z2화합물(이때, Z2는 Q-Sp-SS-W이며, 이때 Sp 및 W는 상기 정의된 바와 같고; Q는 =H2NHNCO-, =H2NHNCS-, =H2NHNCONH-, =H2NHNCSNH-, 또는 =H2NO-임)과 함께 pH 4.0-6.0 및 4°-40℃ 온도의 수성 완충액내에서 1-48시간 동안 반응시켜 하기 일반식의 화합물:Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(H)=Z2]m(상기 식에서, Alk1, Sp1, Ar, Sp2, 및 Alk2, Z3및 m은 상기 정의된 바와 같고, Z2는 Q-Sp-SS-W이며, 이때 Sp 및 W는 상기 정의된 바와 같고; Q는 =NHNCO-, =NHNCS-, =NHNCONH-, =NHNCSNH-, 또는 =NO-임)을 생성하는 것으로 구성되는 방법.
- 제10항에 있어서, Sp1은 -O- 또는 결합이고, Alk1은 결합, 또는 분지 또는 비분지 (C1-C10)알킬렌 연쇄이며, 단 Alk1이 결합이면 Sp1이 결합이고, Z1은 (C1-C5)알킬이고, Z2는 칼리케아미신 N-아세틸 감마 디메틸 히드라지드인 세포독성 약물 컨쥬게이트.
- 하기 일반식:Z3[CO-Alk1-Sp1-Ar-Sp2-Alk2-C(Z1)=Z2]m(상기 식에서 Z3는 사람 P67.6(h-P67.6)이고 m은 0임)의 단백질 부형제.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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