JPH0234922B2 - - Google Patents
Info
- Publication number
- JPH0234922B2 JPH0234922B2 JP56185469A JP18546981A JPH0234922B2 JP H0234922 B2 JPH0234922 B2 JP H0234922B2 JP 56185469 A JP56185469 A JP 56185469A JP 18546981 A JP18546981 A JP 18546981A JP H0234922 B2 JPH0234922 B2 JP H0234922B2
- Authority
- JP
- Japan
- Prior art keywords
- therapeutic agent
- respiratory diseases
- rifampicin
- amino
- trans
- 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.)
- Expired - Lifetime
Links
- 239000003814 drug Substances 0.000 claims description 22
- 229960001225 rifampicin Drugs 0.000 claims description 17
- 208000023504 respiratory system disease Diseases 0.000 claims description 16
- 229940124597 therapeutic agent Drugs 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- GUQRKZPMVLRXLT-UHFFFAOYSA-N n-cyclohexylhydroxylamine Chemical compound ONC1CCCCC1 GUQRKZPMVLRXLT-UHFFFAOYSA-N 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 2
- NIQIPYGXPZUDDP-UHFFFAOYSA-N 3-aminocyclohexan-1-ol Chemical compound NC1CCCC(O)C1 NIQIPYGXPZUDDP-UHFFFAOYSA-N 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims 1
- JQXXHWHPUNPDRT-YOPQJBRCSA-N chembl1332716 Chemical compound O([C@](C1=O)(C)O\C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)/C=C\C=C(C)/C(=O)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CCN(C)CC1 JQXXHWHPUNPDRT-YOPQJBRCSA-N 0.000 description 16
- 239000003242 anti bacterial agent Substances 0.000 description 9
- 229940088710 antibiotic agent Drugs 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 206010036790 Productive cough Diseases 0.000 description 7
- 208000024794 sputum Diseases 0.000 description 7
- 210000003802 sputum Anatomy 0.000 description 7
- QNVKOSLOVOTXKF-UHFFFAOYSA-N 4-[(2-amino-3,5-dibromophenyl)methylamino]cyclohexan-1-ol;hydron;chloride Chemical compound Cl.NC1=C(Br)C=C(Br)C=C1CNC1CCC(O)CC1 QNVKOSLOVOTXKF-UHFFFAOYSA-N 0.000 description 6
- 229960000985 ambroxol hydrochloride Drugs 0.000 description 6
- 229960002335 bromhexine hydrochloride Drugs 0.000 description 5
- YRSGDLIATOURQO-UHFFFAOYSA-N ethyl 4-acetyl-5-oxohexanoate Chemical compound CCOC(=O)CCC(C(C)=O)C(C)=O YRSGDLIATOURQO-UHFFFAOYSA-N 0.000 description 5
- 210000004072 lung Anatomy 0.000 description 5
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 4
- JBDGDEWWOUBZPM-XYPYZODXSA-N ambroxol Chemical compound NC1=C(Br)C=C(Br)C=C1CN[C@@H]1CC[C@@H](O)CC1 JBDGDEWWOUBZPM-XYPYZODXSA-N 0.000 description 4
- 229960005174 ambroxol Drugs 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical class C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 description 4
- 206010057190 Respiratory tract infections Diseases 0.000 description 3
- 229960000723 ampicillin Drugs 0.000 description 3
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 3
- 229960003870 bromhexine Drugs 0.000 description 3
- 206010006451 bronchitis Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003172 expectorant agent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- JBDGDEWWOUBZPM-UHFFFAOYSA-N 4-[(2-amino-3,5-dibromophenyl)methylamino]-1-cyclohexanol Chemical compound NC1=C(Br)C=C(Br)C=C1CNC1CCC(O)CC1 JBDGDEWWOUBZPM-UHFFFAOYSA-N 0.000 description 2
- 206010006458 Bronchitis chronic Diseases 0.000 description 2
- 201000004813 Bronchopneumonia Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000004100 Oxytetracycline Substances 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 229960003022 amoxicillin Drugs 0.000 description 2
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 201000009267 bronchiectasis Diseases 0.000 description 2
- -1 cephalolidine Chemical compound 0.000 description 2
- 208000007451 chronic bronchitis Diseases 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 229940000425 combination drug Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229960003276 erythromycin Drugs 0.000 description 2
- 230000003419 expectorant effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229940066491 mucolytics Drugs 0.000 description 2
- 229960000625 oxytetracycline Drugs 0.000 description 2
- 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 description 2
- 235000019366 oxytetracycline Nutrition 0.000 description 2
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 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 description 2
- 229940126585 therapeutic drug Drugs 0.000 description 2
- HUEKLXFWKUTJBP-RYUDHWBXSA-N (1S,3S)-3-[(2-amino-3,5-dibromophenyl)methyl-methylamino]cyclohexan-1-ol Chemical compound O[C@@H]1C[C@H](CCC1)N(C)CC1=C(C(=CC(=C1)Br)Br)N HUEKLXFWKUTJBP-RYUDHWBXSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
- 208000032376 Lung infection Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- JQXXHWHPUNPDRT-KCFDLMDRSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(Z)-(4-methylpiperazin-1-yl)iminomethyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate Chemical compound CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c(O)c(\C=N/N4CCN(C)CC4)c(NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C JQXXHWHPUNPDRT-KCFDLMDRSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960004308 acetylcysteine Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 229960004399 carbocisteine Drugs 0.000 description 1
- 229960000603 cefalotin Drugs 0.000 description 1
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000010227 cup method (microbiological evaluation) Methods 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 206010062952 diffuse panbronchiolitis Diseases 0.000 description 1
- 229940066493 expectorants Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 230000004199 lung function Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229940124709 respiratory disease therapeutics Drugs 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 229940000634 serratiopeptidase Drugs 0.000 description 1
- 108010038132 serratiopeptidase Proteins 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP56185469A JPS5888311A (ja) | 1981-11-20 | 1981-11-20 | 呼吸器疾患治療剤 |
IT8249521A IT8249521A0 (it) | 1981-11-20 | 1982-11-18 | Composizioni farmaceutiche contenenti idrossicicloesilammine da usare nel trattamento di malattie respiratorie |
FR8219443A FR2516795A1 (fr) | 1981-11-20 | 1982-11-19 | Medicament pour le traitement des maladies respiratoires comprenant un medicament contre les maladies respiratoires et une hydroxycyclohexylamine ou un de ses sels |
GB08233146A GB2110087B (en) | 1981-11-20 | 1982-11-19 | Treatment of respiratory diseases |
DE19823242796 DE3242796A1 (de) | 1981-11-20 | 1982-11-19 | Arzneimittel zur behandlung von erkrankungen der atmungsorgane |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP56185469A JPS5888311A (ja) | 1981-11-20 | 1981-11-20 | 呼吸器疾患治療剤 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5888311A JPS5888311A (ja) | 1983-05-26 |
JPH0234922B2 true JPH0234922B2 (it) | 1990-08-07 |
Family
ID=16171315
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP56185469A Granted JPS5888311A (ja) | 1981-11-20 | 1981-11-20 | 呼吸器疾患治療剤 |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPS5888311A (it) |
DE (1) | DE3242796A1 (it) |
FR (1) | FR2516795A1 (it) |
GB (1) | GB2110087B (it) |
IT (1) | IT8249521A0 (it) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0138020B1 (de) * | 1983-09-17 | 1992-06-03 | Dr. Karl Thomae GmbH | Antiadhäsive Prophylactica und Arzneimittel enthaltend ein sekretolytisch wirksames Benzylaminderivat |
CN106478524B (zh) * | 2016-10-11 | 2018-09-11 | 合肥久诺医药科技有限公司 | 一种盐酸氨溴索杂质标准品的制备方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE795585A (fr) * | 1972-02-17 | 1973-08-16 | Thomae Gmbh Dr K | Nouveau medicament pulmonaire |
DE3034975C2 (de) * | 1980-09-17 | 1986-11-27 | Dr. Karl Thomae Gmbh, 7950 Biberach | Arzneimittelkombination zur Behandlung infektiöser Atemwegerkrankungen |
-
1981
- 1981-11-20 JP JP56185469A patent/JPS5888311A/ja active Granted
-
1982
- 1982-11-18 IT IT8249521A patent/IT8249521A0/it unknown
- 1982-11-19 GB GB08233146A patent/GB2110087B/en not_active Expired
- 1982-11-19 DE DE19823242796 patent/DE3242796A1/de not_active Ceased
- 1982-11-19 FR FR8219443A patent/FR2516795A1/fr active Pending
Also Published As
Publication number | Publication date |
---|---|
IT8249521A0 (it) | 1982-11-18 |
GB2110087A (en) | 1983-06-15 |
GB2110087B (en) | 1985-02-13 |
JPS5888311A (ja) | 1983-05-26 |
FR2516795A1 (fr) | 1983-05-27 |
DE3242796A1 (de) | 1983-06-01 |
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