JPS6362493B2

JPS6362493B2 -

Info

Publication number: JPS6362493B2
Authority: JP; Japan
Prior art keywords: peak; spectrum; band; compound; acid
Prior art date: 1983-01-31
Legal status : Expired

Application number

JP1296283A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5916826A (ja

Priority date

1983-01-31

Filing date

1983-01-31

Publication date

1988-12-02

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=11819877&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JPS6362493(B2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1983-01-31 Application filed filed Critical

1983-01-31 Priority to JP1296283A priority Critical patent/JPS5916826A/ja

1984-01-28 Publication of JPS5916826A publication Critical patent/JPS5916826A/ja

1988-12-02 Publication of JPS6362493B2 publication Critical patent/JPS6362493B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 21
208000014085 Chronic respiratory disease Diseases 0.000 claims description 15
238000010521 absorption reaction Methods 0.000 claims description 14
238000001228 spectrum Methods 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
238000004455 differential thermal analysis Methods 0.000 claims description 8
238000001237 Raman spectrum Methods 0.000 claims description 7
238000000862 absorption spectrum Methods 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
238000000634 powder X-ray diffraction Methods 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 claims description 4
230000000704 physical effect Effects 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
229940119177 germanium dioxide Drugs 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims 1
229920000642 polymer Polymers 0.000 description 32
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 15
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239000013078 crystal Substances 0.000 description 8
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000204031 Mycoplasma Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
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125000000082 organogermanium group Chemical class 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
206010035664 Pneumonia Diseases 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000012790 confirmation Methods 0.000 description 2
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229910052751 metal Inorganic materials 0.000 description 2
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
NLIJOIUVZBYQRS-UHFFFAOYSA-N 3-trichlorogermylpropanoic acid Chemical compound OC(=O)CC[Ge](Cl)(Cl)Cl NLIJOIUVZBYQRS-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
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241000894006 Bacteria Species 0.000 description 1
206010006458 Bronchitis chronic Diseases 0.000 description 1
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206010009126 Chronic respiratory failure Diseases 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
206010014561 Emphysema Diseases 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
241000202946 Mycoplasma pulmonis Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Natural products N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
239000004105 Penicillin G potassium Substances 0.000 description 1
BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
206010035039 Piloerection Diseases 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
238000001069 Raman spectroscopy Methods 0.000 description 1
241000606701 Rickettsia Species 0.000 description 1
241000282887 Suidae Species 0.000 description 1
239000004182 Tylosin Substances 0.000 description 1
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241000700605 Viruses Species 0.000 description 1
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231100000403 acute toxicity Toxicity 0.000 description 1
239000008272 agar Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
230000037444 atrophy Effects 0.000 description 1
IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 description 1
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SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
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150000004820 halides Chemical class 0.000 description 1
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238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
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239000000314 lubricant Substances 0.000 description 1
239000002075 main ingredient Substances 0.000 description 1
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-1 organogermanium compound Chemical class 0.000 description 1
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
HQOJMTATBXYHNR-UHFFFAOYSA-M thallium(I) acetate Chemical compound [Tl+].CC([O-])=O HQOJMTATBXYHNR-UHFFFAOYSA-M 0.000 description 1
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WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 description 1
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