NZ534613A - Methods of simultaneously treating ocular rosacea and acne rosacea with a tetracycline compound - Google Patents
Methods of simultaneously treating ocular rosacea and acne rosacea with a tetracycline compoundInfo
- Publication number
- NZ534613A NZ534613A NZ534613A NZ53461303A NZ534613A NZ 534613 A NZ534613 A NZ 534613A NZ 534613 A NZ534613 A NZ 534613A NZ 53461303 A NZ53461303 A NZ 53461303A NZ 534613 A NZ534613 A NZ 534613A
- Authority
- NZ
- New Zealand
- Prior art keywords
- hydrogen
- amino
- halogen
- dimethylamino
- use according
- Prior art date
Links
- 239000004098 Tetracycline Substances 0.000 title claims abstract description 151
- 235000019364 tetracycline Nutrition 0.000 title claims abstract description 151
- -1 tetracycline compound Chemical class 0.000 title claims abstract description 146
- 229960002180 tetracycline Drugs 0.000 title claims abstract description 133
- 229930101283 tetracycline Natural products 0.000 title claims abstract description 133
- 201000004700 rosacea Diseases 0.000 title claims abstract description 80
- 206010072139 Ocular rosacea Diseases 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title description 35
- 230000003115 biocidal effect Effects 0.000 claims abstract description 44
- 239000003814 drug Substances 0.000 claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 238000007910 systemic administration Methods 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 419
- 239000001257 hydrogen Substances 0.000 claims description 419
- 150000002431 hydrogen Chemical group 0.000 claims description 184
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 110
- 229910052736 halogen Inorganic materials 0.000 claims description 103
- 150000002367 halogens Chemical class 0.000 claims description 100
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 96
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 57
- 150000003522 tetracyclines Chemical class 0.000 claims description 56
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 125000004442 acylamino group Chemical group 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 31
- SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 claims description 23
- 229960003722 doxycycline Drugs 0.000 claims description 23
- 230000001937 non-anti-biotic effect Effects 0.000 claims description 23
- 208000010217 blepharitis Diseases 0.000 claims description 22
- 239000012954 diazonium Substances 0.000 claims description 22
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 21
- FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 claims description 20
- 210000002966 serum Anatomy 0.000 claims description 20
- 229960004023 minocycline Drugs 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 8
- 239000003242 anti bacterial agent Substances 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- HSEMFIZWXHQJAE-UHFFFAOYSA-N Amide-Hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 238000013268 sustained release Methods 0.000 claims description 5
- 239000012730 sustained-release form Substances 0.000 claims description 5
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 claims description 5
- 238000011200 topical administration Methods 0.000 claims description 5
- 239000004100 Oxytetracycline Substances 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 claims description 4
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 claims description 4
- 229960000625 oxytetracycline Drugs 0.000 claims description 4
- 235000019366 oxytetracycline Nutrition 0.000 claims description 4
- GUXHBMASAHGULD-SEYHBJAFSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1([C@H]2O)=C(Cl)C=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O GUXHBMASAHGULD-SEYHBJAFSA-N 0.000 claims description 3
- FMTDIUIBLCQGJB-UHFFFAOYSA-N Demethylchlortetracyclin Natural products C1C2C(O)C3=C(Cl)C=CC(O)=C3C(=O)C2=C(O)C2(O)C1C(N(C)C)C(O)=C(C(N)=O)C2=O FMTDIUIBLCQGJB-UHFFFAOYSA-N 0.000 claims description 3
- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 claims description 3
- 229960002398 demeclocycline Drugs 0.000 claims description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 3
- MWUTTXATIMURBN-VSAOOKSHSA-N (4aS,5aS,6S,12aR)-3,6,10,11-tetrahydroxy-6-methyl-1,12-dioxo-4a,5,5a,12a-tetrahydro-4H-tetracene-2-carboxamide Chemical compound C[C@]1(O)[C@H]2C[C@H]3CC(O)=C(C(N)=O)C(=O)[C@H]3C(=O)C2=C(O)c2c(O)cccc12 MWUTTXATIMURBN-VSAOOKSHSA-N 0.000 claims description 2
- 239000004099 Chlortetracycline Substances 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229960004475 chlortetracycline Drugs 0.000 claims description 2
- 235000019365 chlortetracycline Nutrition 0.000 claims description 2
- BVFDLIAWTKFZQD-JXVDNWKRSA-N cmt-8 Chemical compound O=C1C2=C(O)C=CC=C2C(C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)C[C@@H]1C2O BVFDLIAWTKFZQD-JXVDNWKRSA-N 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- SGKRLCUYIXIAHR-NLJUDYQYSA-N (4r,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-NLJUDYQYSA-N 0.000 claims 1
- 241001303601 Rosacea Species 0.000 claims 1
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- 238000010255 intramuscular injection Methods 0.000 claims 1
- 239000007927 intramuscular injection Substances 0.000 claims 1
- 238000010253 intravenous injection Methods 0.000 claims 1
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/65—Tetracyclines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Organic Chemistry (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Ophthalmology & Optometry (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37314102P | 2002-04-16 | 2002-04-16 | |
| PCT/US2003/011686 WO2003088906A2 (en) | 2002-04-16 | 2003-04-16 | Methods of simultaneously treating ocular rosacea and acne rosacea |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ534613A true NZ534613A (en) | 2007-07-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ534613A NZ534613A (en) | 2002-04-16 | 2003-04-16 | Methods of simultaneously treating ocular rosacea and acne rosacea with a tetracycline compound |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7008631B2 (cg-RX-API-DMAC10.html) |
| EP (2) | EP2368557A1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP2005523313A (cg-RX-API-DMAC10.html) |
| KR (1) | KR20050005444A (cg-RX-API-DMAC10.html) |
| AU (1) | AU2003230935B2 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2476792A1 (cg-RX-API-DMAC10.html) |
| NZ (1) | NZ534613A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2003088906A2 (cg-RX-API-DMAC10.html) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2447008A1 (en) * | 2001-04-05 | 2002-10-24 | Collagenex Pharmaceuticals, Inc. | Controlled delivery of tetracycline compounds and tetracycline derivatives |
| US7211267B2 (en) * | 2001-04-05 | 2007-05-01 | Collagenex Pharmaceuticals, Inc. | Methods of treating acne |
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| US20040092491A1 (en) * | 2002-11-09 | 2004-05-13 | The Research Foundation Of State University Of New York | Method of treating sepsis-induced ARDS |
-
2003
- 2003-04-16 WO PCT/US2003/011686 patent/WO2003088906A2/en not_active Ceased
- 2003-04-16 CA CA002476792A patent/CA2476792A1/en not_active Abandoned
- 2003-04-16 EP EP11152602A patent/EP2368557A1/en not_active Withdrawn
- 2003-04-16 KR KR10-2004-7016366A patent/KR20050005444A/ko not_active Ceased
- 2003-04-16 AU AU2003230935A patent/AU2003230935B2/en not_active Ceased
- 2003-04-16 US US10/414,808 patent/US7008631B2/en not_active Expired - Fee Related
- 2003-04-16 NZ NZ534613A patent/NZ534613A/en not_active IP Right Cessation
- 2003-04-16 JP JP2003585659A patent/JP2005523313A/ja active Pending
- 2003-04-16 EP EP03724047A patent/EP1494681A4/en not_active Ceased
Also Published As
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| JP2005523313A (ja) | 2005-08-04 |
| WO2003088906A2 (en) | 2003-10-30 |
| AU2003230935B2 (en) | 2008-08-07 |
| EP1494681A4 (en) | 2008-08-06 |
| US20030229055A1 (en) | 2003-12-11 |
| EP1494681A2 (en) | 2005-01-12 |
| EP2368557A1 (en) | 2011-09-28 |
| KR20050005444A (ko) | 2005-01-13 |
| WO2003088906A3 (en) | 2004-02-26 |
| CA2476792A1 (en) | 2003-10-30 |
| AU2003230935A1 (en) | 2003-11-03 |
| US7008631B2 (en) | 2006-03-07 |
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