JP2003503420A5 - - Google Patents
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- Publication number
- JP2003503420A5 JP2003503420A5 JP2001507061A JP2001507061A JP2003503420A5 JP 2003503420 A5 JP2003503420 A5 JP 2003503420A5 JP 2001507061 A JP2001507061 A JP 2001507061A JP 2001507061 A JP2001507061 A JP 2001507061A JP 2003503420 A5 JP2003503420 A5 JP 2003503420A5
- Authority
- JP
- Japan
- Prior art keywords
- diketopiperazine
- active agent
- insulin
- complex
- composition
- Prior art date
- 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.)
- Granted
Links
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 36
- 238000000034 method Methods 0.000 description 32
- 239000013543 active substance Substances 0.000 description 23
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 18
- 102000004877 Insulin Human genes 0.000 description 17
- 108090001061 Insulin Proteins 0.000 description 17
- 229940125396 insulin Drugs 0.000 description 17
- 239000011859 microparticle Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 239000003623 enhancer Substances 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 210000004877 mucosa Anatomy 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- BBNKIRVUCQNAQR-FETIZUMASA-N (e)-4-[4-[(2s,5s)-5-[4-[[(e)-3-carboxyprop-2-enoyl]amino]butyl]-3,6-dioxopiperazin-2-yl]butylamino]-4-oxobut-2-enoic acid Chemical group OC(=O)\C=C\C(=O)NCCCC[C@@H]1NC(=O)[C@H](CCCCNC(=O)\C=C\C(O)=O)NC1=O BBNKIRVUCQNAQR-FETIZUMASA-N 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 229940094417 fumaryl diketopiperazine Drugs 0.000 description 3
- QIQCZROILFZKAT-UHFFFAOYSA-N tetracarbon dioxide Chemical group O=C=C=C=C=O QIQCZROILFZKAT-UHFFFAOYSA-N 0.000 description 3
- 125000000349 (Z)-3-carboxyprop-2-enoyl group Chemical group O=C([*])/C([H])=C([H])\C(O[H])=O 0.000 description 2
- -1 glutaryl Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 description 1
- SKHMHSCEONTQTF-UHFFFAOYSA-N 6-thiophen-3-ylquinolin-2-amine Chemical compound C1=CC2=NC(N)=CC=C2C=C1C=1C=CSC=1 SKHMHSCEONTQTF-UHFFFAOYSA-N 0.000 description 1
- 108010000817 Leuprolide Proteins 0.000 description 1
- 108010016076 Octreotide Proteins 0.000 description 1
- 102000003982 Parathyroid hormone Human genes 0.000 description 1
- 108090000445 Parathyroid hormone Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 1
- 229960003773 calcitonin (salmon synthetic) Drugs 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 1
- 229960004338 leuprorelin Drugs 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229960002700 octreotide Drugs 0.000 description 1
- 239000000199 parathyroid hormone Substances 0.000 description 1
- 229960001319 parathyroid hormone Drugs 0.000 description 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 108010068072 salmon calcitonin Proteins 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14143399P | 1999-06-29 | 1999-06-29 | |
| US60/141,433 | 1999-06-29 | ||
| PCT/US2000/017984 WO2001000654A2 (en) | 1999-06-29 | 2000-06-29 | Purification and stabilization of peptide and proteins in pharmaceutical agents |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010209301A Division JP5774828B2 (ja) | 1999-06-29 | 2010-09-17 | ペプチドおよびタンパク質の薬学的因子の精製および安定化 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003503420A JP2003503420A (ja) | 2003-01-28 |
| JP2003503420A5 true JP2003503420A5 (https=) | 2007-08-23 |
| JP4713798B2 JP4713798B2 (ja) | 2011-06-29 |
Family
ID=22495668
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001507061A Expired - Fee Related JP4713798B2 (ja) | 1999-06-29 | 2000-06-29 | ペプチドおよびタンパク質の薬学的因子の精製および安定化 |
| JP2010209301A Expired - Lifetime JP5774828B2 (ja) | 1999-06-29 | 2010-09-17 | ペプチドおよびタンパク質の薬学的因子の精製および安定化 |
| JP2012230348A Expired - Fee Related JP5798999B2 (ja) | 1999-06-29 | 2012-10-17 | ペプチドおよびタンパク質の薬学的因子の精製および安定化 |
| JP2014139069A Ceased JP2014221794A (ja) | 1999-06-29 | 2014-07-04 | ペプチドおよびタンパク質の薬学的因子の精製および安定化 |
| JP2015245237A Pending JP2016117722A (ja) | 1999-06-29 | 2015-12-16 | ペプチドおよびタンパク質の薬学的因子の精製および安定化 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010209301A Expired - Lifetime JP5774828B2 (ja) | 1999-06-29 | 2010-09-17 | ペプチドおよびタンパク質の薬学的因子の精製および安定化 |
| JP2012230348A Expired - Fee Related JP5798999B2 (ja) | 1999-06-29 | 2012-10-17 | ペプチドおよびタンパク質の薬学的因子の精製および安定化 |
| JP2014139069A Ceased JP2014221794A (ja) | 1999-06-29 | 2014-07-04 | ペプチドおよびタンパク質の薬学的因子の精製および安定化 |
| JP2015245237A Pending JP2016117722A (ja) | 1999-06-29 | 2015-12-16 | ペプチドおよびタンパク質の薬学的因子の精製および安定化 |
Country Status (11)
| Country | Link |
|---|---|
| US (7) | US6444226B1 (https=) |
| EP (5) | EP1196430B1 (https=) |
| JP (5) | JP4713798B2 (https=) |
| AT (1) | ATE545652T1 (https=) |
| AU (3) | AU779986B2 (https=) |
| CA (1) | CA2377204C (https=) |
| CY (3) | CY1112441T1 (https=) |
| DK (4) | DK1196430T3 (https=) |
| ES (4) | ES2569916T3 (https=) |
| PT (2) | PT1808438E (https=) |
| WO (1) | WO2001000654A2 (https=) |
Cited By (13)
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| US8623817B2 (en) | 2008-08-11 | 2014-01-07 | Mannkind Corporation | Method of treating diabetes type 2 by administering ultrarapid acting insulin |
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| US9364436B2 (en) | 2011-06-17 | 2016-06-14 | Mannkind Corporation | High capacity diketopiperazine microparticles and methods |
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| US9675674B2 (en) | 2004-08-23 | 2017-06-13 | Mannkind Corporation | Diketopiperazine salts for drug delivery and related methods |
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