CA2156065A1 - Immunomodulateurs a base d'uree et d'amide macrocyclique - Google Patents

Immunomodulateurs a base d'uree et d'amide macrocyclique

Info

Publication number: CA2156065A1
Authority: CA; Canada
Prior art keywords: ethyl; compound; configuration; och3; och2c
Prior art date: 1993-03-17
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.): Abandoned

Application number

CA002156065A

Other languages

English (en)

Inventor

Rolf Wagner

Jay R. Luly

Yat Sun Or

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.)

Abbott Laboratories

Original Assignee

Individual

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.)

1993-03-17

Filing date

1994-03-11

Publication date

1994-09-29

1994-03-11 Application filed by Individual filed Critical Individual

1994-09-29 Publication of CA2156065A1 publication Critical patent/CA2156065A1/fr

Status Abandoned legal-status Critical Current

Links

150000001408 amides Chemical class 0.000 title claims abstract description 16
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 12
239000004202 carbamide Substances 0.000 title description 5
239000002955 immunomodulating agent Substances 0.000 title description 2
229940121354 immunomodulator Drugs 0.000 title description 2
150000002148 esters Chemical class 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 17
229940002612 prodrug Drugs 0.000 claims abstract description 11
239000000651 prodrug Substances 0.000 claims abstract description 11
230000001506 immunosuppresive effect Effects 0.000 claims abstract description 9
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
230000002519 immonomodulatory effect Effects 0.000 claims abstract description 7
229940121375 antifungal agent Drugs 0.000 claims abstract description 6
230000002441 reversible effect Effects 0.000 claims abstract description 6
239000002246 antineoplastic agent Substances 0.000 claims abstract description 5
206010059866 Drug resistance Diseases 0.000 claims abstract description 4
230000000843 anti-fungal effect Effects 0.000 claims abstract description 4
230000001028 anti-proliverative effect Effects 0.000 claims abstract description 4
229940044683 chemotherapy drug Drugs 0.000 claims abstract description 4
230000000845 anti-microbial effect Effects 0.000 claims abstract description 3
230000003110 anti-inflammatory effect Effects 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 550
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 402
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 191
-1 3-phenyl-phenyl Chemical group 0.000 claims description 188
238000000034 method Methods 0.000 claims description 144
239000001257 hydrogen Substances 0.000 claims description 69
229910052739 hydrogen Inorganic materials 0.000 claims description 69
125000003118 aryl group Chemical group 0.000 claims description 67
125000000623 heterocyclic group Chemical group 0.000 claims description 42
229910052757 nitrogen Inorganic materials 0.000 claims description 42
125000000217 alkyl group Chemical group 0.000 claims description 38
150000002431 hydrogen Chemical group 0.000 claims description 37
150000003254 radicals Chemical class 0.000 claims description 37
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
150000002367 halogens Chemical class 0.000 claims description 28
229910006069 SO3H Inorganic materials 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
125000005842 heteroatom Chemical group 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
239000004593 Epoxy Substances 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 16
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 13
239000003937 drug carrier Substances 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
125000004103 aminoalkyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 7
210000000056 organ Anatomy 0.000 claims description 7
238000002054 transplantation Methods 0.000 claims description 7
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 6
210000001519 tissue Anatomy 0.000 claims description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
201000004624 Dermatitis Diseases 0.000 claims description 5
210000004072 lung Anatomy 0.000 claims description 5
125000000464 thioxo group Chemical group S=* 0.000 claims description 5
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
210000003734 kidney Anatomy 0.000 claims description 4
210000004185 liver Anatomy 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000006413 ring segment Chemical group 0.000 claims description 4
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 3
206010015150 Erythema Diseases 0.000 claims description 3
206010018364 Glomerulonephritis Diseases 0.000 claims description 3
229910007161 Si(CH3)3 Inorganic materials 0.000 claims description 3
210000004087 cornea Anatomy 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
210000002216 heart Anatomy 0.000 claims description 3
230000003463 hyperproliferative effect Effects 0.000 claims description 3
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
230000000414 obstructive effect Effects 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
208000023504 respiratory system disease Diseases 0.000 claims description 3
125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical group CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 2
208000002874 Acne Vulgaris Diseases 0.000 claims description 2
208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 claims description 2
208000023275 Autoimmune disease Diseases 0.000 claims description 2
208000015943 Coeliac disease Diseases 0.000 claims description 2
206010009900 Colitis ulcerative Diseases 0.000 claims description 2
208000011231 Crohn disease Diseases 0.000 claims description 2
206010014989 Epidermolysis bullosa Diseases 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
208000030836 Hashimoto thyroiditis Diseases 0.000 claims description 2
206010020751 Hypersensitivity Diseases 0.000 claims description 2
206010061218 Inflammation Diseases 0.000 claims description 2
206010051606 Necrotising colitis Diseases 0.000 claims description 2
206010034277 Pemphigoid Diseases 0.000 claims description 2
241000721454 Pemphigus Species 0.000 claims description 2
206010036774 Proctitis Diseases 0.000 claims description 2
201000004681 Psoriasis Diseases 0.000 claims description 2
229910006067 SO3−M Inorganic materials 0.000 claims description 2
206010053615 Thermal burn Diseases 0.000 claims description 2
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
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208000012339 Vascular injury Diseases 0.000 claims description 2
206010053648 Vascular occlusion Diseases 0.000 claims description 2
206010047112 Vasculitides Diseases 0.000 claims description 2
206010047115 Vasculitis Diseases 0.000 claims description 2
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 2
206010000496 acne Diseases 0.000 claims description 2
230000007815 allergy Effects 0.000 claims description 2
208000004631 alopecia areata Diseases 0.000 claims description 2
208000010668 atopic eczema Diseases 0.000 claims description 2
208000000594 bullous pemphigoid Diseases 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
210000001198 duodenum Anatomy 0.000 claims description 2
201000001564 eosinophilic gastroenteritis Diseases 0.000 claims description 2
231100000321 erythema Toxicity 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
206010020718 hyperplasia Diseases 0.000 claims description 2
230000004054 inflammatory process Effects 0.000 claims description 2
230000003903 intestinal lesions Effects 0.000 claims description 2
201000011486 lichen planus Diseases 0.000 claims description 2
208000008585 mastocytosis Diseases 0.000 claims description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
201000006417 multiple sclerosis Diseases 0.000 claims description 2
210000003205 muscle Anatomy 0.000 claims description 2
206010028417 myasthenia gravis Diseases 0.000 claims description 2
208000004995 necrotizing enterocolitis Diseases 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
210000000496 pancreas Anatomy 0.000 claims description 2
201000006195 perinatal necrotizing enterocolitis Diseases 0.000 claims description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
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210000000329 smooth muscle myocyte Anatomy 0.000 claims description 2
201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
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QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
208000009329 Graft vs Host Disease Diseases 0.000 claims 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
208000028185 Angioedema Diseases 0.000 claims 1
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CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
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VNYSSYRCGWBHLG-AMOLWHMGSA-M leukotriene B4(1-) Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC([O-])=O VNYSSYRCGWBHLG-AMOLWHMGSA-M 0.000 claims 1
ILMAWLHMLHOTQU-UHFFFAOYSA-N methyl 2-(7h-purin-6-ylsulfanyl)acetate Chemical compound COC(=O)CSC1=NC=NC2=C1NC=N2 ILMAWLHMLHOTQU-UHFFFAOYSA-N 0.000 claims 1
150000002678 macrocyclic compounds Chemical class 0.000 abstract description 5
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 49
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230000008733 trauma Effects 0.000 description 1
KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000002255 vaccination Methods 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
239000004474 valine Substances 0.000 description 1
230000003966 vascular damage Effects 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
201000005539 vernal conjunctivitis Diseases 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
201000001862 viral hepatitis Diseases 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
210000003905 vulva Anatomy 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
150000004798 β-ketoamides Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Immunology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Transplantation (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CA002156065A 1993-03-17 1994-03-11 Immunomodulateurs a base d'uree et d'amide macrocyclique Abandoned CA2156065A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US3295893A	1993-03-17	1993-03-17
US08/032,958		1993-03-17
US14941993A	1993-11-09	1993-11-09
US08/149,419		1993-11-09

Publications (1)

Publication Number	Publication Date
CA2156065A1 true CA2156065A1 (fr)	1994-09-29

Family

ID=26709099

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002156065A Abandoned CA2156065A1 (fr)	1993-03-17	1994-03-11	Immunomodulateurs a base d'uree et d'amide macrocyclique

Country Status (4)

Country	Link
EP (1)	EP0689545A4 (fr)
JP (1)	JPH08507789A (fr)
CA (1)	CA2156065A1 (fr)
WO (1)	WO1994021642A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6376517B1 (en) *	1998-08-14	2002-04-23	Gpi Nil Holdings, Inc.	Pipecolic acid derivatives for vision and memory disorders
US6121257A (en) *	1999-03-31	2000-09-19	Abbott Laboratories	Sulfamate containing macrocyclic immunomodulators
GB0125443D0 (en)	2001-10-23	2001-12-12	Novartis Ag	Organic Compounds
ES2428354T3 (es)	2002-09-18	2013-11-07	Trustees Of The University Of Pennsylvania	Rapamicina para usar en la inhibición o prevención de la neovascularización coroidea
US7920906B2 (en)	2005-03-10	2011-04-05	Dexcom, Inc.	System and methods for processing analyte sensor data for sensor calibration
JP2007505932A (ja)	2003-09-18	2007-03-15	マクサイト，インコーポレイテッド	経強膜送達
US9247900B2 (en)	2004-07-13	2016-02-02	Dexcom, Inc.	Analyte sensor
US8989833B2 (en)	2004-07-13	2015-03-24	Dexcom, Inc.	Transcutaneous analyte sensor
WO2006127694A2 (fr)	2004-07-13	2006-11-30	Dexcom, Inc.	Detecteur d'analyte
TW200637552A (en) *	2005-01-20	2006-11-01	Array Biopharma Inc	Macrocyclic analogs for the treatment of immunoregulatory disorders and respiratory diseases
WO2006086750A1 (fr)	2005-02-09	2006-08-17	Macusight, Inc.	Formulations liquides pour le traitement de maladies ou affections
US8492400B2 (en)	2006-02-09	2013-07-23	Santen Pharmaceutical Co., Ltd.	Stable formulations, and methods of their preparation and use
CN101443004B (zh)	2006-03-23	2013-03-06	参天制药株式会社	用于与血管通透性有关的疾病或病症的制剂

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5250678A (en) *	1991-05-13	1993-10-05	Merck & Co., Inc.	O-aryl, O-alkyl, O-alkenyl and O-alkynylmacrolides having immunosuppressive activity
US5565560A (en) *	1991-05-13	1996-10-15	Merck & Co., Inc.	O-Aryl,O-alkyl,O-alkenyl and O-alkynylmacrolides having immunosuppressive activity
CA2103454C (fr) *	1991-09-05	2004-11-02	Jay R. Luly	Immunomodulateurs macrocycliques

1994
- 1994-03-11 CA CA002156065A patent/CA2156065A1/fr not_active Abandoned
- 1994-03-11 WO PCT/US1994/002692 patent/WO1994021642A1/fr not_active Ceased
- 1994-03-11 JP JP6521135A patent/JPH08507789A/ja active Pending
- 1994-03-11 EP EP94910923A patent/EP0689545A4/fr not_active Withdrawn

Also Published As

Publication number	Publication date
EP0689545A1 (fr)	1996-01-03
JPH08507789A (ja)	1996-08-20
WO1994021642A1 (fr)	1994-09-29
EP0689545A4 (fr)	1996-04-24

Legal Events

Date	Code	Title	Description
1999-03-11	FZDE	Dead

Publication	Publication Date	Title
US5457111A (en)	1995-10-10	Macrocyclic immunomodulators
CA2175215C (fr)	2008-06-03	Analogues semi-synthetiques de rapamycine (macrolides) utilises comme immunomodulateurs
US5527907A (en)	1996-06-18	Macrolide immunomodulators
US5561228A (en)	1996-10-01	Macrocyclic immunomodulators
US5457194A (en)	1995-10-10	Substituted aliphatic amine-containing macrocyclic immunomodulators
US5604234A (en)	1997-02-18	Substituted thiol macrolactam immunomodulators
US5643918A (en)	1997-07-01	Marcrocyclic amide and urea immunomodulators
US5541189A (en)	1996-07-30	Substituted aliphatic amine-containing macrocyclic immunomodulators
US5708002A (en)	1998-01-13	Macrocyclic immunomodulators
EP0689545A1 (fr)	1996-01-03	IMMUNOREGULATEURS A l'AMIDE MACROCYCLIQUE ET A L'UREE
US5561137A (en)	1996-10-01	Thio-heterocyclic macrolactam immunomodulators
US5561140A (en)	1996-10-01	Substituted alicyclic amine-containing macrocyclic immunomodulators
US5561139A (en)	1996-10-01	Substituted alicyclic-aliphatic amine-containing macrocyclic immunomodulators
AU669337C (en)	1997-08-28	Macrocyclic immunomodulators