BG107091A - Нови пиперазинови производни - Google Patents
Нови пиперазинови производни Download PDFInfo
- Publication number
- BG107091A BG107091A BG107091A BG10709102A BG107091A BG 107091 A BG107091 A BG 107091A BG 107091 A BG107091 A BG 107091A BG 10709102 A BG10709102 A BG 10709102A BG 107091 A BG107091 A BG 107091A
- Authority
- BG
- Bulgaria
- Prior art keywords
- alkyl
- amino
- aryl
- aminocarbonyl
- alkylamino
- Prior art date
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- 150000004885 piperazines Chemical class 0.000 title description 2
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 200
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 342
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 311
- -1 hydroxy, hydroxysulfonyl Chemical group 0.000 claims description 194
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 109
- 229910052799 carbon Inorganic materials 0.000 claims description 84
- 125000005281 alkyl ureido group Chemical group 0.000 claims description 72
- 125000003282 alkyl amino group Chemical group 0.000 claims description 71
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 63
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 61
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 59
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 59
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 57
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 41
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 40
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 37
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 36
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 36
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 32
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 31
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
- 235000013877 carbamide Nutrition 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 241000282838 Lama Species 0.000 claims description 28
- 235000002198 Annona diversifolia Nutrition 0.000 claims description 26
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 26
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 25
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
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- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 16
- 150000003672 ureas Chemical class 0.000 claims description 16
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- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 14
- 206010061218 Inflammation Diseases 0.000 claims description 13
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 13
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- 102000004500 CCR1 Receptors Human genes 0.000 claims description 12
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- 102000004127 Cytokines Human genes 0.000 claims description 12
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
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- 150000001412 amines Chemical class 0.000 claims description 11
- 125000001769 aryl amino group Chemical group 0.000 claims description 11
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 206010046851 Uveitis Diseases 0.000 claims description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 8
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- 231100000283 hepatitis Toxicity 0.000 claims description 7
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 7
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- 201000006417 multiple sclerosis Diseases 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 201000008482 osteoarthritis Diseases 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 7
- 230000000552 rheumatic effect Effects 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 201000008827 tuberculosis Diseases 0.000 claims description 7
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- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
- 208000006386 Bone Resorption Diseases 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 6
- 208000031886 HIV Infections Diseases 0.000 claims description 6
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- 241000713340 Human immunodeficiency virus 2 Species 0.000 claims description 6
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- 206010027202 Meningitis bacterial Diseases 0.000 claims description 6
- 206010027236 Meningitis fungal Diseases 0.000 claims description 6
- 208000034578 Multiple myelomas Diseases 0.000 claims description 6
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 6
- 201000009904 bacterial meningitis Diseases 0.000 claims description 6
- 230000024279 bone resorption Effects 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 201000010056 fungal meningitis Diseases 0.000 claims description 6
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- 206010020718 hyperplasia Diseases 0.000 claims description 6
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- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
- 241000701161 unidentified adenovirus Species 0.000 claims description 6
- 241001529453 unidentified herpesvirus Species 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
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- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 5
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- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
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- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 101000825726 Homo sapiens Structural maintenance of chromosomes protein 4 Proteins 0.000 claims description 2
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- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 235000009508 confectionery Nutrition 0.000 claims description 2
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- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 14
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
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- HQMLIDZJXVVKCW-REOHCLBHSA-N L-alaninamide Chemical compound C[C@H](N)C(N)=O HQMLIDZJXVVKCW-REOHCLBHSA-N 0.000 claims 1
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- NSFFHOGKXHRQEW-AIHSUZKVSA-N thiostrepton Chemical compound C([C@]12C=3SC=C(N=3)C(=O)N[C@H](C(=O)NC(/C=3SC[C@@H](N=3)C(=O)N[C@H](C=3SC=C(N=3)C(=O)N[C@H](C=3SC=C(N=3)[C@H]1N=1)[C@@H](C)OC(=O)C3=CC(=C4C=C[C@H]([C@@H](C4=N3)O)N[C@H](C(N[C@@H](C)C(=O)NC(=C)C(=O)N[C@@H](C)C(=O)N2)=O)[C@@H](C)CC)[C@H](C)O)[C@](C)(O)[C@@H](C)O)=C\C)[C@@H](C)O)CC=1C1=NC(C(=O)NC(=C)C(=O)NC(=C)C(N)=O)=CS1 NSFFHOGKXHRQEW-AIHSUZKVSA-N 0.000 claims 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- LXIKEPCNDFVJKC-QXMHVHEDSA-N tenidap Chemical compound C12=CC(Cl)=CC=C2N(C(=O)N)C(=O)\C1=C(/O)C1=CC=CS1 LXIKEPCNDFVJKC-QXMHVHEDSA-N 0.000 description 1
- 229960003676 tenidap Drugs 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
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Classifications
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D307/20—Oxygen atoms
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- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US19378900P | 2000-03-31 | 2000-03-31 | |
PCT/IB2001/000375 WO2001072728A2 (en) | 2000-03-31 | 2001-03-14 | Novel piperazine derivatives |
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BG107091A true BG107091A (bg) | 2003-04-30 |
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BG107091A BG107091A (bg) | 2000-03-31 | 2002-09-12 | Нови пиперазинови производни |
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US (2) | US6649611B2 (xx) |
EP (1) | EP1268455A2 (xx) |
JP (1) | JP2003528867A (xx) |
KR (1) | KR20020084273A (xx) |
CN (1) | CN1450999A (xx) |
AP (1) | AP2002002637A0 (xx) |
AR (1) | AR033813A1 (xx) |
AU (1) | AU2001239469A1 (xx) |
BG (1) | BG107091A (xx) |
BR (1) | BR0109703A (xx) |
CA (1) | CA2404626A1 (xx) |
CZ (1) | CZ20023154A3 (xx) |
DZ (1) | DZ3306A1 (xx) |
EA (1) | EA006079B1 (xx) |
EE (1) | EE200200567A (xx) |
HR (1) | HRP20020785A2 (xx) |
HU (1) | HUP0300567A3 (xx) |
IL (1) | IL151923A0 (xx) |
IS (1) | IS6546A (xx) |
MA (1) | MA26887A1 (xx) |
MX (1) | MXPA02009645A (xx) |
NO (1) | NO20024649L (xx) |
NZ (1) | NZ521290A (xx) |
OA (1) | OA12239A (xx) |
PA (1) | PA8514401A1 (xx) |
PE (1) | PE20011309A1 (xx) |
PL (1) | PL358618A1 (xx) |
SK (1) | SK13652002A3 (xx) |
SV (1) | SV2002000356A (xx) |
TN (1) | TNSN01047A1 (xx) |
UA (1) | UA73553C2 (xx) |
WO (1) | WO2001072728A2 (xx) |
YU (1) | YU69902A (xx) |
ZA (1) | ZA200207827B (xx) |
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DE60213958T2 (de) | 2001-02-27 | 2007-08-30 | Migenix Corp., San Diego | Aryl-n-cyanoguanidine derivate und deren verwendung |
CN1529699A (zh) * | 2001-06-20 | 2004-09-15 | �Ʒ� | 新的磺酸衍生物 |
US6812230B2 (en) * | 2001-08-07 | 2004-11-02 | Schering Aktiengesellschaft | Non-peptide CCR1 receptor antagonists for the treatment of progressive renal fibrosis |
US7655658B2 (en) | 2001-08-10 | 2010-02-02 | Palatin Technologies, Inc. | Thieno [2,3-D]pyrimidine-2,4-dione melanocortin-specific compounds |
US7732451B2 (en) * | 2001-08-10 | 2010-06-08 | Palatin Technologies, Inc. | Naphthalene-containing melanocortin receptor-specific small molecule |
US7718802B2 (en) | 2001-08-10 | 2010-05-18 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
AU2002331064B2 (en) * | 2001-08-10 | 2007-08-23 | Palatin Technologies, Inc. | Peptidomimetics of biologically active metallopeptides |
US7354923B2 (en) * | 2001-08-10 | 2008-04-08 | Palatin Technologies, Inc. | Piperazine melanocortin-specific compounds |
US7456184B2 (en) | 2003-05-01 | 2008-11-25 | Palatin Technologies Inc. | Melanocortin receptor-specific compounds |
JP2005507923A (ja) * | 2001-10-22 | 2005-03-24 | ファイザー・プロダクツ・インク | Ccr1受容体アンタゴニスト活性を有するピペラジン誘導体 |
AU2003202495B2 (en) * | 2002-01-11 | 2006-07-20 | Sankyo Company, Limited | Amino alcohol derivative or phosphonic acid derivative and medicinal composition containing these |
US20050256130A1 (en) * | 2002-06-12 | 2005-11-17 | Chemocentryx, Inc. | Substituted piperazines |
EP1531822B1 (en) | 2002-06-12 | 2009-08-05 | ChemoCentryx Inc | 1-aryl-4-substituted piperazine derivatives for use as ccr1 antagonists for the treatment of inflammation and immune disorders |
US7589199B2 (en) * | 2002-06-12 | 2009-09-15 | Chemocentryx, Inc. | Substituted piperazines |
US7842693B2 (en) * | 2002-06-12 | 2010-11-30 | Chemocentryx, Inc. | Substituted piperazines |
US20040087571A1 (en) * | 2002-10-30 | 2004-05-06 | Pfizer Inc | Methods of using CCR1 antagonists as immunomodulatory agents |
US20040116441A1 (en) * | 2002-10-30 | 2004-06-17 | Pfizer Inc | Methods of using sulfonic acid derivatives |
US20040092529A1 (en) * | 2002-10-30 | 2004-05-13 | Pfizer Inc | Methods of using piperazine derivatives |
BR0317244A (pt) * | 2002-12-13 | 2005-11-01 | Pfizer Prod Inc | Derivados de piperazina contendo fósforo como antagonistas ccr1 |
US7727991B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific single acyl piperazine compounds |
US7968548B2 (en) | 2003-05-01 | 2011-06-28 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine compounds with diamine groups |
US7727990B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine and keto-piperazine compounds |
SI21507A (sl) | 2003-05-16 | 2004-12-31 | LEK farmacevtska dru�ba d.d. | Postopek za pripravo spojin z ace inhibitornim delovanjem |
AU2004264724A1 (en) * | 2003-08-14 | 2005-02-24 | Pfizer Inc. | Piperazine derivatives for the treatment of HIV infections |
FR2864080B1 (fr) * | 2003-12-23 | 2006-02-03 | Sanofi Synthelabo | Derives de 1-piperazine-et-1-homopiperazine-carboxylates, leur preparation et leur application en therapeutique |
CN1938029A (zh) * | 2004-02-06 | 2007-03-28 | 舍林股份公司 | 具有趋化因子抑制作用的哌嗪衍生物及其在治疗多发性骨髓瘤中的应用 |
KR101182619B1 (ko) | 2004-02-24 | 2012-09-18 | 상꾜 가부시키가이샤 | 아미노 알코올 화합물 |
SE0400441D0 (sv) | 2004-02-25 | 2004-02-25 | Active Biotech Ab | Novel Benzofurans and Indols |
FR2866888B1 (fr) * | 2004-02-26 | 2006-05-05 | Sanofi Synthelabo | Derives de alkylpiperazine- et alkylhomopiperazine- carboxylates, leur preparation et leur application en therapeutique |
EP1720545B1 (en) * | 2004-03-03 | 2014-10-29 | ChemoCentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
US7435831B2 (en) * | 2004-03-03 | 2008-10-14 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
US7709484B1 (en) | 2004-04-19 | 2010-05-04 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
US7829589B2 (en) * | 2005-06-10 | 2010-11-09 | Elixir Pharmaceuticals, Inc. | Sulfonamide compounds and uses thereof |
US20060293370A1 (en) * | 2005-06-10 | 2006-12-28 | Saunders Jeffrey O | Sulfonamide compounds and uses thereof |
WO2007136790A2 (en) * | 2006-05-18 | 2007-11-29 | Mannkind Corporation | Intracellular kinase inhibitors |
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WO2008036285A1 (en) * | 2006-09-18 | 2008-03-27 | Energex Systems, Inc. | Method of treating viral infections with ultraviolet light |
SI2521715T1 (sl) * | 2010-01-05 | 2014-10-30 | Actelion Pharmaceuticals Ltd. | Piperazini kot sredstva proti malariji |
US9439884B2 (en) * | 2011-05-26 | 2016-09-13 | Beth Israel Deaconess Medical Center, Inc. | Methods for the treatment of immune disorders |
US9730941B2 (en) | 2012-06-07 | 2017-08-15 | Beth Israel Deaconess Medical Center, Inc. | Methods and compositions for the inhibition of Pin1 |
WO2016011265A2 (en) | 2014-07-17 | 2016-01-21 | Beth Israel Deaconess Medical Center, Inc. | Biomarkers for pin1-associated disorders |
WO2016145186A1 (en) | 2015-03-12 | 2016-09-15 | Beth Israel Deaconess Medical Center, Inc. | Enhanced atra-related compounds for the treatment of proliferative diseases, autoimmune diseases, and addiction conditions |
US11166912B2 (en) | 2016-03-03 | 2021-11-09 | Ctt Pharma Inc. | Orally administrable composition |
US11518739B2 (en) | 2017-08-15 | 2022-12-06 | Inflazome Limited | Sulfonamide carboxamide compounds |
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US11667613B2 (en) | 2019-09-26 | 2023-06-06 | Novartis Ag | Antiviral pyrazolopyridinone compounds |
CN113754566B (zh) * | 2021-10-14 | 2023-03-21 | 山东新华制药股份有限公司 | Oab-14合成工艺 |
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BE640616A (xx) * | 1962-12-19 | |||
US3492397A (en) * | 1967-04-07 | 1970-01-27 | Warner Lambert Pharmaceutical | Sustained release dosage in the pellet form and process thereof |
US3538214A (en) * | 1969-04-22 | 1970-11-03 | Merck & Co Inc | Controlled release medicinal tablets |
US4060596A (en) * | 1972-09-30 | 1977-11-29 | Sony Corporation | Method of making goethite powder |
US4173626A (en) * | 1978-12-11 | 1979-11-06 | Merck & Co., Inc. | Sustained release indomethacin |
JP2651043B2 (ja) * | 1990-07-10 | 1997-09-10 | 麒麟麦酒株式会社 | ジフェニルメチルピペラジン誘導体 |
FR2724656B1 (fr) * | 1994-09-15 | 1996-12-13 | Adir | Nouveaux derives du benzopyranne, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
US6207665B1 (en) | 1997-06-12 | 2001-03-27 | Schering Aktiengesellschaft | Piperazine derivatives and their use as anti-inflammatory agents |
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- 2001-03-14 OA OA1200200301A patent/OA12239A/en unknown
- 2001-03-14 UA UA2002097590A patent/UA73553C2/uk unknown
- 2001-03-14 SK SK1365-2002A patent/SK13652002A3/sk not_active Application Discontinuation
- 2001-03-14 CN CN01807616A patent/CN1450999A/zh active Pending
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- 2001-03-14 BR BR0109703-2A patent/BR0109703A/pt not_active IP Right Cessation
- 2001-03-14 AU AU2001239469A patent/AU2001239469A1/en not_active Abandoned
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- 2001-03-29 PE PE2001000295A patent/PE20011309A1/es not_active Application Discontinuation
- 2001-03-29 US US09/821,322 patent/US6649611B2/en not_active Expired - Fee Related
- 2001-03-29 AR ARP010101511A patent/AR033813A1/es unknown
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- 2001-03-30 TN TNTNSN01047A patent/TNSN01047A1/fr unknown
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2002
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- 2002-09-12 BG BG107091A patent/BG107091A/bg unknown
- 2002-09-24 MA MA26838A patent/MA26887A1/fr unknown
- 2002-09-27 NO NO20024649A patent/NO20024649L/no not_active Application Discontinuation
- 2002-09-30 ZA ZA200207827A patent/ZA200207827B/xx unknown
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